Abstract
The enantioselective synthesis of β-amino-β-ferrocenyl alcohols,
a new class of chiral ferrocene derivatives suitable for the elaboration
of auxiliaries and ligands for asymmetric synthesis, can be efficiently
achieved by the catalytic asymmetric dihydroxylation of 1-ferrocenylalkenes,
followed by the regio- and stereoselective substitution of the hydroxy
group adjacent to the ferrocene moiety by nitrogen nucleophiles.
En route to these compounds, several previously unknown metallocene
derivatives such as α-ferrocenyl epoxides, interannularly
cyclopalladated ferrocenyloxazolines, and α-amino-α-ferrocenyl
acids have been obtained. The first examples of an organocatalytic
approach to the enantioselective synthesis of chiral ferrocenes
are also presented.
1 Introduction
2 The Quest for a Stable α-Ferrocenyl Epoxide
3 The Asymmetric Dihydroxylation Route to β-Amino-β-ferrocenyl
Alcohols
4 Applications of Chiral Auxiliaries and Ligands Derived from β-Amino-β-ferrocenyl
Alcohols to Asymmetric Synthesis
4.1 Asymmetric Diels-Alder Reactions
4.2 Asymmetric Palladium-Catalyzed Allylic Substitution Reactions
4.3 Catalytic Enantioselective Nucleophilic Additions to Aldehydes
5 Interannular Cyclopalladation of 4-Ferrocenyloxazolines
5.1 Synthesis and Structural Characterization of Cyclopalladated
4-Ferrocenyl-1,3-oxazolines
5.2 Applications of Interannularly Cyclopalladated 4-Ferrocenyl-1,3-oxazolines
in Catalysis
6 Enantioselective Synthesis of Novel Ferrocenyl Amino Acids
7 The Kinetic Resolution Approach to Planar Chiral Ferrocenes
8 Enantioselective Organocatalytic Synthesis of Chiral Ferrocenes
9 Summary and Outlook
Key words
amino alcohols - asymmetric catalysis - epoxides - ferrocenes - palladacycles
References 1 ICREA Junior Researcher at the University
of Barcelona
2a Richards CJ.
Locke AJ.
Tetrahedron: Asymmetry
1998,
9:
2377
2b Sutcliffe OB.
Bryce MR.
Tetrahedron:
Asymmetry
2003,
14:
2297
2c Barbaro P.
Bianchini C.
Giambastiani G.
Parisel SL.
Coord. Chem. Rev.
2004,
248:
2131
2d Arrayás RG.
Adrio J.
Carretero JC.
Angew. Chem. Int. Ed.
2006,
45:
7674
3a Ferrocenes. Homogeneous Catalysis, Organic
Synthesis and Materials Chemistry
Togni A.
Hayashi T.
VCH;
Weinheim:
1995.
3b Ferrocenes.
From Materials and Chemistry to Biology: Ligands, Materials and Biomolecules
Stepnicka P.
Wiley-VCH;
Weinheim:
2008.
4a van Staveren DR.
Metzler-Nolte N.
Chem. Rev.
2004,
104:
5931
4b Fouda MRF.
Abd-Elhazer MM.
Abdelsamaia RA.
Labib AA.
Appl. Organomet. Chem.
2007,
21:
613
5a Canas M.
Poch M.
Verdaguer X.
Moyano A.
Pericàs MA.
Riera A.
Tetrahedron
Lett.
1991,
32:
8301
5b Castejón P.
Pastó M.
Moyano A.
Pericàs MA.
Riera A.
Tetrahedron Lett.
1995,
36:
3019
5c Solà L.
Vidal-Ferran A.
Moyano A.
Pericàs MA.
Riera A.
Tetrahedron: Asymmetry
1997,
8:
1559
5d Vidal A.
Moyano A.
Pericàs MA.
Riera A.
J. Org. Chem.
1997,
62:
4970
5e Solà L.
Reddy KS.
Vidal-Ferran A.
Moyano A.
Pericàs MA.
Riera A.
Alvarez-Larena A.
Piniella JF.
J.
Org. Chem.
1998,
63:
7078
5f Reddy KS.
Solà L.
Moyano A.
Pericàs MA.
Riera A.
Alvarez-Larena A.
Piniella JF.
J. Org. Chem.
1999,
64:
3969
6a Poch M.
Alcón M.
Moyano A.
Pericàs MA.
Riera A.
Tetrahedron
Lett.
1993,
34:
7781
6b Alcón M.
Canas M.
Poch M.
Moyano A.
Pericàs MA.
Riera A.
Tetrahedron
Lett.
1995,
35:
1589
6c Pastó M.
Moyano A.
Pericàs MA.
Riera A.
Tetrahedron:
Asymmetry
1995,
6:
2329
6d Pastó M.
Moyano A.
Pericàs MA.
Riera A.
J.
Org. Chem.
1997,
62:
8425
6e Castejón P.
Moyano A.
Pericàs MA.
Riera A.
Chem.
Eur. J.
1996,
2:
1001
6f Aguilar N.
Moyano A.
Pericàs MA.
Riera A.
J. Org. Chem.
1998,
63:
3560
6g Medina E.
Moyano A.
Pericàs MA.
Riera A.
J. Org. Chem.
1998,
63:
8574
6h Aguilar N.
Moyano A.
Pericàs MA.
Riera A.
Tetrahedron
Lett.
1999,
40:
3193
6i Martín R.
Islas G.
Moyano A.
Pericàs MA.
Riera A.
Tetrahedron
2001,
57:
6367
7a Hanson RM.
Sharpless KB.
J. Org. Chem.
1986,
51:
1922
7b Gao Y.
Hanson RM.
Klunder JM.
Ko SY.
Masamune H.
Sharpless KB.
J.
Am. Chem. Soc.
1987,
109:
5765
7c Katsuki T.
Martín VS.
Org. React.
1996,
48:
1
7d Katsuki T. In Comprehensive Asymmetric Catalysis
Vol.
2:
Jacobsen EN.
Pfaltz A.
Yamamoto H.
Springer;
Berlin:
1999.
p.621
8a Schlögl K.
Monatsh. Chem.
1957,
88:
601
8b Schlögl K.
Mohar A.
Monatsh. Chem.
1962,
93:
861
8c Zmuda H.
Tetrahedron
Lett.
1979,
43:
4221
9a Patti A.
Nicolosi G.
Tetrahedron:
Asymmetry
2000,
11:
815
9b Patti A.
Nicolosi G.
Tetrahedron: Asymmetry
2000,
11:
3687
10a Schlögl K.
Egger H.
Monatsh.
Chem.
1963,
94:
376
10b Egger H.
Schlögl K.
J. Organomet. Chem.
1964,
2:
398
11a Sevenair JP.
Lewis DH.
Ponder BW.
J.
Org. Chem.
1972,
37:
4061
11b Schwink L.
Knochel P.
Eberle T.
Okuda J.
Organometallics
1998,
17:
7
12a Hill EA.
Richards JH.
J. Am. Chem. Soc.
1961,
83:
3840
12b Kreiter CG.
Maasbol A.
Anet FAL.
Kaesz HD.
Winstein S.
J. Am. Chem. Soc.
1966,
88:
3442
12c Gokel GW.
Marquading D.
Ugi IK.
J. Org. Chem.
1972,
37:
3052
13a Aggarwal VK.
Abdel-Rahman H.
Jones RVH.
Lee HY.
Reid BD.
J.
Am. Chem. Soc.
1994,
116:
5973
13b Aggarwal VK.
Abdel-Rahman H.
Fan L.
Jones
RVH.
Standen MCH.
Chem. Eur.
J.
1996,
2:
212
13c Aggarwal VK.
Synlett
1998,
329
14 Catasús M.
Moyano A.
Aggarwal VK.
Tetrahedron Lett.
2002,
43:
3475
15 Aggarwal VK.
Alonso E.
Hynd G.
Lydon KM.
Palmer MJ.
Porcelloni M.
Studley JR.
Angew.
Chem. Int. Ed.
2001,
40:
1430
16a Kolb HC.
Sharpless KB. In Transition Metals
for Organic Synthesis
Beller M.
Bolm C.
Wiley-VCH;
New
York:
.
16b O’Brien P.
Angew. Chem. Int. Ed.
1999,
38:
236
17a Li G.
Chang H.-T.
Sharpless KB.
Angew. Chem., Int. Ed. Engl.
1996,
35:
451
17b Bruncko M.
Schlingoff G.
Sharpless KB.
Angew.
Chem., Int. Ed. Engl.
1997,
36:
1483
17c Laxma Reddy K.
Sharpless KB.
J.
Am. Chem. Soc.
1998,
120:
1207
17d Song CE.
Oh CR.
Roh EJ.
Lee S.
Choi JH.
Tetrahedron: Asymmetry
1999,
10:
671
18a Jacobsen EN.
Markó I.
Mungall WS.
Schröder G.
Sharpless KB.
J.
Am. Chem. Soc.
1988,
110:
1968
18b Lohray BB.
Tetrahedron: Asymmetry
1992,
3:
1317
18c Kolb HC.
VanNieuwenhenze MS.
Sharpless KB.
Chem. Rev.
1994,
94:
2483
18d Cha JK.
Kim N.-S.
Chem. Rev.
1995,
95:
1761
18e Markó IE.
Svendsen JS. In Comprehensive Asymmetric Catalysis
Vol.
2:
Jacobsen EN.
Pfaltz A.
Yamamoto H.
Springer;
Berlin:
1999.
p.713
19 Jary WG.
Baumgartner J.
Tetrahedron: Asymmetry
1998,
9:
2081
20 Crispino GA.
Jeong K.-S.
Kolb HC.
Wang Z.-M.
Xu D.
Sharpless KB.
J. Org. Chem.
1993,
58:
3785
21 Horspool WM.
Sutherland RG.
Can.
J. Chem.
1968,
46:
3543
22 Berger RK.
Biehl ER.
Reeves PC.
J. Org. Chem.
1974,
39:
477
23 Catasús M.
Bueno A.
Moyano A.
Maestro MA.
Mahía J.
J.
Organomet. Chem.
2002,
642:
212
24 Bueno A.
Moreno RM.
Moyano A.
Tetrahedron: Asymmetry
2005,
16:
1763
25 Vanhessche KPM.
Sharpless KB.
J.
Org. Chem.
1996,
61:
7978
26 Moreno RM.
Bueno A.
Moyano A.
J.
Org. Chem.
2006,
71:
2528
27 Moreno RM.
Rosol M.
Moyano A.
Tetrahedron: Asymmetry
2006,
17:
1089
28 Patti A.
Lotz M.
Knochel P.
Tetrahedron:
Asymmetry
2001,
12:
3375
29a Noyori R.
Kitamura H.
Angew.
Chem., Int. Ed. Engl.
1991,
30:
49
29b Soai K.
Niwa S.
Chem. Rev.
1992,
92:
833
29c Blaser H.-U.
Chem.
Rev.
1992,
92:
935
29d Deloux S.
Srebnik M.
Chem. Rev.
1993,
93:
763
29e Chiral
Auxiliaries and Ligands in Asymmetric Synthesis
Seyden-Penne J.
Wiley;
Chichester:
1992.
29f Ayer DJ.
Prakash I.
Schaad DR.
Chem. Rev.
1996,
62:
835
29g Catalytic
Asymmetric Synthesis
2nd ed.:
Ojima I.
Wiley-VCH;
New York:
2000.
30 Bommarius AS.
Schwarm M.
Kottenhahn M.
Hutchmacher K.
Drauz K.
Tetrahedron: Asymmetry
1995,
6:
2851
31a Kloukowsky C.
Pouilhes P.
Langlois Y.
J. Am. Chem. Soc.
1990,
112:
6672
31b Sibi MP.
Deshpande PK.
La Loggia AJ.
Christensen JW.
Tetrahedron
Lett.
1995,
36:
8961
31c Kauffmann GD.
Harris RL.
Drow BRP.
Parsons RL.
Perti JA.
Magnus NA.
Fortunak JM.
Confalone RN.
Nugent WA.
Org. Lett.
2000,
2:
3119
31d Chrisman W.
Camara JN.
Marcellini K.
Singaram B.
Goralshi CT.
Hasha PL.
Rudolf PR.
Nicholson LW.
Borodychuk KK.
Tetrahedron Lett.
2001,
42:
5805
32a Matsunaga H.
Kimura KI.
Ishizuka T.
Haratake M.
Kunieda T.
Tetrahedron Lett.
1991,
32:
7715
32b Nakamura T.
Hashimoto N.
Ishizuka T.
Kunieda T.
Tetrahedron Lett.
1997,
38:
559
32c Clariana J.
García-Granda S.
Gotor V.
Gutiérrez-Fernández A.
Luna A.
Moreno-Mañas M.
Vallribera A.
Tetrahedron: Asymmetry
2000,
11:
4549
33 Schwink L.
Knochel P.
Tetrahedron Lett.
1997,
38:
3711
34a Asymmetric Diels-Alder Reactions
Taschner MJ.
JAI
Press;
Greenwich:
1989.
34b Rück-Braun K.
Kunz H.
Chiral Auxiliaries in Cycloadditions
Wiley;
New
York:
1999.
34c Lewis
Acids in Organic Synthesis
Yamamoto H.
Wiley-VCH;
New
York:
2001.
35 Evans DA.
Chapman KT.
Bisaha J.
J.
Am. Chem. Soc.
1988,
110:
1238
36 Martinelli MJ.
J.
Org. Chem.
1990,
55:
5065
37a Trost BM.
Van Vranken DL.
Chem.
Rev.
1996,
96:
395
37b Pfaltz A.
Lautens M. In Comprehensive
Asymmetric Catalysis
Vol. 2:
Jacobsen
EN.
Pfaltz A.
Yamamoto H.
Springer;
Berlin:
1999.
p.833
37c Helmchen G.
Pfaltz A.
Acc. Chem. Res.
2000,
33:
336
37d Trost BM.
Chulbom C. In Catalytic Asymmetric Synthesis
2nd
ed.:
Ojima I.
Wiley-VCH;
New
York:
2000.
p.593
38a Brown JM.
Hulmes DI.
Guiry PJ.
Tetrahedron
1994,
50:
4993
38b Von Matt P.
Lloyd-Jones GC.
Mindis ABE.
Pfaltz A.
Macko L.
Neuburger M.
Zehnder M.
Rüegger H.
Pregosin PS.
Helv. Chim. Acta
1995,
36:
265
39 Moreno RM.
Bueno A.
Moyano A.
J.
Organomet. Chem.
2002,
660:
62
40 Von Matt P.
Pfaltz A.
Angew. Chem., Int. Ed. Engl.
1993,
32:
566
41 Wiese B.
Helmchen G.
Tetrahedron Lett.
1994,
35:
8595
42 Kudis S.
Helmchen G.
Angew. Chem. Int. Ed.
1998,
37:
3047
43 Sennhen P.
Gabler B.
Helmchen G.
Tetrahedron
Lett.
1994,
35:
8595
44a Aratani T.
Pure
Appl. Chem.
1985,
57:
1839
44b Desimoni G.
Quadrelli P.
Righetti PP.
Tetrahedron
1990,
46:
2927
44c Bolm C.
Bienewald F.
Angew. Chem., Int. Ed. Engl.
1995,
34:
2640
44d Fleischer R.
Braun M.
Synlett
1998,
1441
44e Cogan DA.
Liu G.
Kim K.
Backes DJ.
Ellman JA.
J. Am. Chem. Soc.
1998,
120:
8011
44f Dossetter AG.
Jamison TF.
Jacobsen EN.
Angew. Chem. Int. Ed.
1999,
38:
2398
44g Ruck TR.
Jacobsen EN.
J.
Am. Chem. Soc.
2002,
124:
2882
44h Gao X.
Hall DG.
J. Am. Chem. Soc.
2003,
125:
9038
45 Li Z.
Liu G.
Zheng Z.
Chen H.
Tetrahedron
2000,
56:
7187
46a Flores-López LZ.
Parra-Hake M.
Somanathan R.
Walsh PJ.
Organometallics
2000,
12:
2153
46b Gama A.
Flores-López LZ.
Aguirre G.
Parra-Hake M.
Somanathan R.
Cole T.
Tetrahedron:
Asymmetry
2005,
16:
1167
47 Mori A.
Inoue S. In Comprehensive
Asymmetric Catalysis
Vol. 2:
Jacobsen EN.
Pfaltz A.
Yamamoto H.
Springer;
Berlin:
1999.
p.983
48a Ryu DH.
Corey EJ.
J.
Am. Chem. Soc.
2005,
127:
5384
48b Yamagiwa N.
Tian J.
Matsunaga S.
Shibasaki M.
J. Am. Chem. Soc.
2005,
127:
3413
48c Fuerst DE.
Jacobsen EN.
J.
Am. Chem. Soc.
2005,
127:
8964
48d Lundgren S.
Wingstrand E.
Penhoat M.
Moberg C.
J. Am. Chem. Soc.
2005,
127:
11592
48e Negru M.
Schollmeyer D.
Kunz H.
Angew.
Chem. Int. Ed.
2007,
46:
9939
48f Connon SJ.
Angew. Chem. Int. Ed.
2008,
47:
1176
49a Hayashi M.
Miyamoto Y.
Inoue T.
Oguni N.
49b Hayashi M.
Miyamoto Y.
Inoue T.
Oguni N.
J. Org. Chem.
1993,
58:
1515
49c Hayashi M.
Inoue T.
Miyamoto Y.
Oguni N.
Tetrahedron
1994,
50:
4385
50a Hayashi M.
Inoue T.
Oguni N.
J. Chem. Soc., Chem. Commun.
1994,
341
50b Hayashi M.
Kaneda H.
Oguni N.
Tetrahedron:
Asymmetry
1995,
6:
2511
50c Oguni N.
Tanaka K.
Ishida H.
Synlett
1998,
601
51 Moreno RM.
Moyano A.
Tetrahedron: Asymmetry
2006,
17:
1104
52 Corey EJ.
Barnes-Seeman D.
Lee TW.
Tetrahedron Lett.
1997,
38:
4351
53 Cope AC.
Siekman RW.
J. Am. Chem. Soc.
1965,
87:
3272
54a Ref. 37a
54b Wild SB.
Coord. Chem. Rev.
1997,
166:
291
54c Dupont J.
Pfeffer M.
Spencer J.
Eur.
J. Inorg. Chem.
2001,
1917
54d Djukic J.-P.
Hijazi A.
Flack HD.
Bernardinelli G.
Chem. Soc. Rev.
2008,
37:
406
55a Espinet P.
Esteruelas MA.
Oro LA.
Serrano JL.
Solà E.
Coord. Chem. Rev.
1992,
117:
215
55b Iyer S.
Jayanthi A.
Tetrahedron Lett.
2001,
42:
7877
55c Alonso DA.
Nájera C.
Pacheco MC.
J. Org. Chem.
2002,
67:
5588
55d Cohen F.
Overman LE.
Tetrahedron: Asymmetry
1998,
9:
3213
55e Gruber AS.
Zim D.
Ebeling G.
Monteiro AL.
Dupont J.
Org.
Lett.
2000,
2:
1287
55f Zhao G.
Wang Q.
Mak TCW.
Organometallics
1998,
17:
3437
55g Bosque R.
López C.
Solans X.
Font-Bardia M.
Organometallics
1999,
18:
1267
55h Jautze S.
Seiler P.
Peters R.
Angew.
Chem. Int. Ed.
2007,
46:
1260
56a Pfeffer M.
Rotteveel MA.
Pascal J.
De Cian A.
Fischer J.
J.
Organomet. Chem.
1989,
371:
C21
56b Tao W.
Silverberg JL.
Rheingold AL.
Heck RF.
Organometallics
1989,
8:
2550
56c Nonoyama M.
Hamamura K.
J. Organomet. Chem.
1991,
407:
271
56d Bosque R.
López C.
Sales J.
Solans X.
J. Organomet. Chem.
1994,
483:
61
56e Huo SQ.
Wu YJ.
Zhu Y.
Yang L.
J. Organomet.
Chem.
1994,
470:
17
56f Wu YJ.
J.
Organomet. Chem.
2001,
637-639:
27
56g Pérez S.
López C.
Caubet A.
Bosque R.
Solans X.
Font-Bardía M.
Roig A.
Molins E.
Organometallics
2004,
23:
224
57a Donde Y.
Overman LE.
J.
Am. Chem. Soc.
1999,
121:
2933
57b Overman LE.
Remarchuk TP.
J.
Am. Chem. Soc.
2002,
124:
12
58 Moyano A.
Rosol M.
Moreno RM.
López C.
Maestro MA.
Angew. Chem. Int. Ed.
2005,
44:
1865
59 Rosol M.
PhD Thesis
University
of Barcelona;
Spain:
2006.
60 Murahashi T.
Kurosawa H.
Coord. Chem. Rev.
2002,
321:
207
61a Fuchita Y.
Hisaki K.
Uchiyama T.
J. Organomet. Chem.
1985,
280:
C51
61b Pfeffer M.
Wehman E.
van Koten G.
J.
Organomet. Chem.
1985,
282:
127
61c Balavoine GGA.
Clinet JC.
J.
Organomet. Chem.
1990,
390:
C84
61d Alonso MT.
Juanes O.
de Mendoza J.
Rodríguez-Ubis J.
J.
Organomet. Chem.
1992,
430:
349
62 Ryabov AD.
Chem. Rev.
1990,
90:
403
63 Dupont J.
Consorti CS.
Spencer J.
Chem.
Rev.
2005,
105:
2527
64 Ryabov AD.
Synthesis
1985,
233
65a Bosque R.
López C.
Sales J.
Inorg. Chim. Acta
1996,
244:
141
65b López C.
Bosque R.
Solans X.
Font-Bardía M.
Tramuns D.
Fern G.
Silver J.
J.
Chem. Soc., Dalton Trans.
1994,
3039
66 Troitskaya LL.
Starikova ZA.
Demeschik TV.
Ovseenko ST.
Vorontsov EV.
Sokolov VI.
67 Zhao XM.
Hao XQ.
Liu B.
Zhang ML.
Song MP.
Wu YJ.
J. Organomet. Chem.
2006,
691:
255
68a Heck RF.
Org. React.
1982,
27:
345
68b de Meijere A.
Meyer F.
Angew. Chem., Int. Ed. Engl.
1994,
33:
2379
68c Cabri W.
Candiani I.
Acc. Chem. Res.
1995,
28:
2
68d Reetz MT. In Transition Metal
Catalyzed Reactions
Davies SG.
Murahashi S.-I.
Blackwell Science;
Oxford:
1999.
68e Shibasaki M.
Vogl EM.
68f Beletskaya IP.
Cheprakov AV.
Chem.
Rev.
2000,
100:
3009
68g Phan
NTS.
Van Der Sluys M.
Jones CW.
Adv. Synth. Catal.
2006,
348:
609
69a Park SB.
Alper H.
Org. Lett.
2003,
5:
3209
69b Kondolff I.
Doucet H.
Santelli M.
Tetrahedron
Lett.
2003,
44:
8487
69c Na Y.
Park S.
Han SB.
Han H.
Ko S.
Chang S.
J. Am. Chem. Soc.
2004,
126:
250
69d Pucheault M.
Darses S.
Genet J.-P.
J.
Am. Chem. Soc.
2004,
126:
15256
69e Reetz MT.
de Vries JG.
Chem. Commun.
2004,
1559
69f Xiao J.
Twamley B.
Shreeve
JM.
Org. Lett.
2004,
6:
3845
69g Hansen AL.
Skrydstrup T.
J. Org.
Chem.
2005,
70:
5997
69h Mino T.
Shirae Y.
Sasai Y.
Sakamoto M.
Fujita T.
J. Org. Chem.
2006,
71:
6834
69i Lindh J.
Enquist P.-A.
Pilotti A.
Nilsson P.
Larhed M.
J.
Org. Chem.
2007,
72:
7957
69j Cui J.
Li J.
Zhang Z.-P.
Fu Y.
Liu L.
Guo X.-Q.
J.
Org. Chem.
2007,
72:
9342
69k Kalyani D.
Sanford
MS.
J. Am.
Chem. Soc.
2008,
130:
2150
69l Lipshutz BH.
Taft BR.
Org.
Lett.
2008,
10:
1329
70a Herrmann WA.
Böhm VPW.
Reisinger CP.
J. Organomet. Chem.
1999,
576:
23
70b van der Boom ME.
Milstein D.
Chem. Rev.
2003,
103:
1759
71a Herrmann WA.
Brossmer C.
Öfele K.
Reisinger C.
Riermeier T.
Beller M.
Fisher H.
Angew. Chem., Int. Ed. Engl.
1995,
34:
1844
71b Ohlff M.
Ohlff A.
van der Boom ME.
Milstein D.
J. Am. Chem. Soc.
1997,
119:
11687
71c Shaw BL.
Perera SD.
Staley EA.
Chem. Commun.
1998,
1361
71d Alonso DA.
Nájera C.
Pacheco M.
Org. Lett.
2000,
2:
1823
71e Morales-Morales D.
Redón R.
Yung C.
Jensen CM.
Chem.
Commun.
2000,
1619
71f Peris E.
Mata J.
Loch JA.
Crabtree
RH.
Chem.
Commun.
2001,
201
71g Consorti CS.
Zanini ML.
Leal S.
Ebeling G.
Dupont J.
Org. Lett.
2003,
5:
983
71h Yuan K.
Zhang TK.
Hou XL.
J.
Org. Chem.
2005,
70:
6085
72a Alonso DA.
Nájera C.
Pacheco M.
Adv. Synth.
Catal.
2002,
344:
172
72b Yang F.
Zhang Y.
Zheng R.
Tang J.
He M.
J. Organomet.
Chem.
2002,
651:
146
73 Rosol M.
Moyano A.
J. Organomet. Chem.
2005,
690:
2291
74 Amatore C.
Jutand A.
Acc. Chem. Res.
2000,
33:
314
75a Herrmann WA.
Brossmer C.
Reisinger C.-P.
Riermeyer TH.
Öfele K.
Beller M.
Chem. Eur. J.
1997,
3:
1357
75b Shaw BL.
New J. Chem.
1998,
77
75c Miyazaki F.
Yamaguchi K.
Shibasaki M.
Tetrahedron Lett.
1999,
40:
7379
75d Brunel JM.
Hirlemann M.-H.
Heumann A.
Buono G.
Chem. Commun.
2000,
1869
76a Beletskaya IP.
Kashin AN.
Karlstedt NB.
Mitin AV.
Cheprakov AV.
Kazankov GM.
J. Organomet. Chem.
2001,
622:
89
76b Nowotny M.
Hanefeld U.
van Koningsveld H.
Maschmeyer T.
Chem. Commun.
2000,
1877
76c Böhm VPW.
Herrmann WA.
Chem.
Eur. J.
2001,
7:
4191
76d de Vries AHM.
Mulders JMCA.
Mommers JHM.
Henderickx HJW.
de
Vries JG.
Org. Lett.
2003,
5:
3285
76e Eberhard MR.
Org. Lett.
2004,
6:
2125
76f Consorti CS.
Flores FR.
Dupont J.
77 For a recent critical review on the
nature of the active species in the Heck-Mizoroki coupling,
see ref. 68g.
ortho -palladacycles with alkenes, see:
78a Holton RA.
Tetrahedron Lett.
1977,
4:
355
78b Izumi T.
Watabe H.
Kasahara A.
Bull.
Chem. Soc. Jpn.
1981,
54:
1711
79 Astruc D.
Lu F.
Ruiz Aranzaes J.
Angew. Chem.
Int. Ed.
2005,
44:
7852
80a Foley P.
DiCosimo R.
Whitesides GM.
J. Am. Chem. Soc.
1980,
102:
6713
80b Anton DR.
Crabtree RH.
Organometallics
1983,
2:
855
80c Whitesides GM.
Hackett M.
Brainard RL.
Lavalleye J.-PPM.
Sowinski AF.
Izumi AN.
Moore SS.
Brown DW.
Staudt EM.
Organometallics
1985,
4:
1819
81 Hollis TK.
Overman LE.
82a Overman LE.
Owen CE.
Pavan MM.
Richards CJ.
Org.
Lett.
2003,
5:
1809
82b Kang J.
Kim TH.
Yew KH.
Lee WK.
Tetrahedron: Asymmetry
2003,
14:
415
82c Anderson
CE.
Overman LE.
J.
Am. Chem. Soc.
2003,
125:
12412
82d Kirsch SF.
Overman LE.
Watson MP.
J. Org. Chem.
2004,
69:
8101
82e Kirsch SF.
Overman LE.
White NS.
Org. Lett.
2007,
9:
911
82f Watson MP.
Overman LE.
Bergman RG.
J. Am. Chem. Soc.
2007,
129:
5031
82g Nomura H.
Richards CJ.
Chem. Eur. J.
2007,
13:
10216
82h Jautze S.
Seiler P.
Peters R.
Chem. Eur.
J.
2008,
14:
1430
82i Overman LE.
Roberts SW.
Sneddon HF.
Org. Lett.
2008,
10:
1485
83a Calter M.
Hollis TK.
Overman LE.
Ziller J.
Zipp GG.
J. Org. Chem.
1997,
62:
1449
83b Kang J.
Yew
KH.
Kim TH.
Choi DH.
Tetrahedron
Lett.
2002,
43:
9509
84a Ugi I.
Beck F.
Fetzer U.
Chem. Ber.
1962,
95:
126
84b Schenck TG.
Bosnich B.
J. Am. Chem.
Soc.
1985,
107:
2058
84c Tamura K.
Mizukami H.
Maeda K.
Watanabe H.
Uneyama K.
J.
Org. Chem.
1993,
58:
32
85 36c to (S )-37c catalyzed by a dimeric (di-µ-trifluoroacetate)palladium
complex derived from (R )-N ,N -dimethyl-2-(ferrocenyl)ethylamine occurred
in 47% yield with a 73.5:25.5 enantiomeric ratio. See: Hollis TK.
Overman LE.
Tetrahedron
Lett.
1997,
38:
8837
86a Moriuchi T.
Nomoto A.
Yoshida K.
Ogawa A.
J. Am. Chem. Soc.
2001,
123:
4817
86b Xu Y.
Kraatz H.-B.
Tetrahedron Lett.
2001,
42:
2601
86c Ferber B.
Top S.
Vessières A.
Welter R.
Jaouen G.
Organometallics
2006,
25:
5730
86d James P.
Neudörff J.
Eissmann M.
Jesse P.
Prokop A.
Schmalz H.-G.
Org. Lett.
2006,
8:
2763
86e Baldoli C.
Rigamonti C.
Maiorana S.
Licandro E.
Falciola L.
Mussini PR.
Chem. Eur. J.
2007,
12:
4091
86f Schatzschneider U.
Metzler-Nolte N.
Angew.
Chem. Int. Ed.
2006,
45:
1504
86g Anne A.
Demaille C.
J. Am. Chem. Soc.
2006,
128:
542
86h Lykkesfeldt J.
Morgan E.
Stephan C.
Skovgaard LT.
Moos T.
J.
Biochem. Mol. Toxicol.
2007,
21:
145
86i Freisleben D.
Hauck T.
Sünkel K.
Beck W.
Z. Anorg. Allg. Chem.
2007,
633:
1100
86j Lapic J.
Pavlovic G.
Siebler D.
Heinze K.
Rapic V.
Organometallics
2008,
27:
726
86k Patwa AN.
Gupta S.
Gonnade RG.
Kumar VA.
Bhadbhade MM.
Ganesh KN.
J. Org. Chem.
2008,
73:
1508
86l Fujimoto K.
Kawai H.
Amano M.
Inouye M.
J. Org. Chem.
2008,
73:
5123
87a Jackson RFW.
Turner D.
Block MH.
Synlett
1996,
862
87b Brunner H.
König W.
Nuber B.
Tetrahedron: Asymmetry
1993,
4:
699
88 Maricic S.
Berg U.
Frejd T.
Tetrahedron
2002,
58:
3085
89 Adamczyc M.
Reddy RE.
Rege SD.
Synth. Commun.
2000,
30:
1389
90 Graham PJ.
Lindsey RV.
Parshall GW.
Peterson
ML.
Whitman GM.
J. Am. Chem. Soc.
1957,
79:
3416
91 Dialer H.
Steglich W.
Beck W.
Tetrahedron
2001,
57:
4855
92 Bueno A.
PhD Thesis
University
of Barcelona;
Spain:
2005.
93 Corey EJ.
Link J.-O.
J. Am. Chem. Soc.
1992,
114:
1906
94 Reeve W.
Group RF.
J. Org. Chem.
1967,
32:
122
95 Moreno RM.
Catasús M.
López C.
Moyano A.
Eur. J. Org. Chem.
2008,
2388
96 Choukroun R.
Gervais D.
J. Chem. Soc., Dalton Trans.
1980,
1800
97a Creary X.
Org. Lett.
2002,
4:
2069
97b Harrington
LE.
Vargas-Baca I.
Reginato N.
McGlinchey MJ.
Organometallics
2003,
22:
663
97c Gleiter R.
Bleiholder C.
Rominger F.
Organometallics
2007,
26:
4850
98 Hatakeyama S.
Matsumoto H.
Fukuyama H.
Mukugi Y.
Irie H.
J.
Org. Chem.
1997,
62:
2275
99 Smith AB.
Lee D.
Adams MC.
Kozlowski MC.
Org.
Lett.
2002,
4:
4539
100a Sagan S.
Karogan P.
Lequin O.
Chassaing G.
Lavielle S.
Curr. Med. Chem.
2004,
11:
2799
100b Kuethe JT.
Gauthier DR.
Beutner GL.
Yasuda N.
J.
Org. Chem.
2007,
72:
7469 ;
and references cited therein
101a Marquarding D.
Klusakec H.
Gokel G.
Hoffman P.
Ugi I.
J. Am. Chem. Soc.
1970,
92:
5389
101b Hayashi T.
Kumada M.
Acc. Chem. Res.
1982,
15:
395
101c Sawamura M.
Ito Y.
Chem. Rev.
1992,
92:
857
102a Sammakia T.
Latham HA.
Schaad DR.
J. Org. Chem.
1995,
60:
10
102b Richards CJ.
Damalidis T.
Hibbs DE.
Hursthouse MB.
Synlett
1995,
74
102c Nishibayashi Y.
Uemura S.
Synlett
1995,
79
103 Rebière F.
Riant O.
Ricard L.
Kagan HB.
Angew. Chem., Int. Ed. Engl.
1993,
32:
568
104 Riant O.
Samuel O.
Kagan HB.
J.
Am. Chem. Soc.
1993,
115:
5835
105 Tsukazaki M.
Tinkl M.
Roglans A.
Chapell BJ.
Taylor NJ.
Snieckus V.
J. Am.
Chem. Soc.
1996,
118:
685
106a Maciejewski LA.
Goetgheluck SJ.
Delacroix OA.
Brocard JS.
Tetrahedron: Asymmetry
1996,
6:
1573
106b Fukuzawa S.
Fujimoto K.
Synlett
2001,
1275
106c Taylor CJ.
Roca FX.
Richards CJ.
Synlett
2005,
2159
106d Li H.
Cheng H.
Seow A.
Loh T.
Tetrahedron Lett.
2007,
48:
2209
107 Omedes M.
Gómez-Sal P.
Andriès J.
Moyano A.
Tetrahedron
2008,
64:
3953
108a Norrby PO.
Rasmussen T.
Haller J.
Strassner T.
Houk KN.
J. Am. Chem. Soc.
1999,
121:
10186
108b Ujaque G.
Maseras F.
Lledós A.
J.
Org. Chem.
1997,
62:
7892
109 García J.
Moyano A.
Rosol M.
Tetrahedron
2007,
63:
1907
110 Steffen W.
Laskoski M.
Collins G.
Bunz UHF.
111a VanNieuwhenze MS.
Sharpless KB.
J. Am. Chem. Soc.
1993,
115:
7864
111b Yokomatsu T.
Yamagishi T.
Sada T.
Suemune K.
Shibuya S.
Tetrahedron
1998,
54:
781
111c Rios R.
Jimeno C.
Carroll PJ.
Walsh PJ.
111d Dai W.-M.
Zhang Y.
Zhang Y.
Tetrahedron:
Asymmetry
2004,
15:
525
112 Companyó X.
MSc Thesis
University
of Barcelona;
Spain:
2008.
113a Ogasawara M.
Watanabe S.
Fan L.
Nakajima K.
Takahashi T.
Organometallics
2006,
25:
5201
113b Ogasawara M.
Watanabe S.
Nakajima K.
Takahashi T.
Pure Appl. Chem.
2008,
80:
1109
114 Ruble JC.
Latham HA.
Fu GC.
J.
Am. Chem. Soc.
1997,
119:
1492
115a List B.
J. Am. Chem. Soc.
2000,
122:
9336
115b List B.
Pojarliev P.
Biller WT.
Martin HJ.
J. Am. Chem. Soc.
2002,
124:
827
116a Zhang H.
Ramasastry SSV.
Tanaka F.
Barbas CF.
Adv.
Synth. Catal.
2008,
350:
791
116b Utsumi N.
Zhang H.
Tanaka F.
Barbas CF.
Angew. Chem. Int. Ed.
2007,
46:
1878
116c Ramasastry SSV.
Zhang H.
Tanaka F.
Barbas CF.
J.
Am. Chem. Soc.
2007,
129:
288
116d Zhang H.
Misfud M.
Tanaka F.
Barbas CF.
J. Am.
Chem. Soc.
2006,
128:
9630
116e Cheong PH.-Y.
Zhanh H.
Thayumanavan R.
Tanaka F.
Barbas CF.
Org. Lett.
2006,
8:
811
116f Mitsumori S.
Zhang H.
Cheong PH.-Y.
Houk KN.
Barbas CF.
J. Am. Chem. Soc.
2006,
128:
1040
116g Chowdari NS.
Suri JC.
Barbas CF.
Org. Lett.
2004,
6:
2507
116h Córdova A.
Watanabe S.-I.
Tanaka F.
Barbas CF.
J.
Am. Chem. Soc.
2002,
124:
1866
116i Córdova A.
Notz W.
Zhong G.
Betancour JM.
Barbas CF.
J. Am. Chem. Soc.
2002,
124:
1842
116j Notz W.
Tanaka F.
Watanabe S.-I.
Bui T.
Barbas CF.
J.
Org. Chem.
2003,
68:
9624
116k Dziedzic P.
Ibrahem I.
Córdova A.
Tetrahedron
Lett.
2008,
49:
803
116l Dziedzic P.
Córdova A.
Tetrahedron: Asymmetry
2007,
18:
1033
116m Vesely J.
Ríos R.
Ibrahem I.
Córdova A.
Tetrahedron Lett.
2006,
48:
421
116n Zhao G.-L.
Córdova A.
Tetrahedron Lett.
2006,
47:
7417
116o Ibrahem I.
Córdova A.
Chem. Commun.
2006,
1760
116p Liao W.-W.
Ibrahem I.
Córdova A.
Chem.
Commun.
2006,
674
116q Ibrahem I.
Zou W.
Engqvist M.
Xu Y.
Córdova A.
Chem.
Eur. J.
2005,
11:
7024
116r Córdova A.
Chem. Eur. J.
2004,
10:
1987
117 rac -4-ferrocenyl-4-(2-naphthyl)aminobutanone
in the reaction between (2-naphthyl)ferrocenylimine and
acetone catalyzed by
p -toluenesulfonic
acid. See: Kalenikov EA.
Zh.
Obshch. Khim.
1977,
43:
628
118 Valero G.
Balaguer A.-N.
Moyano A.
Rios R.
Tetrahedron Lett.
2008,
49:
6559
119 Barbas CF.
Angew. Chem. Int. Ed.
2008,
47:
42
120 Bahmanyar S.
Houk KN.
Org. Lett.
2003,
5:
1249
121 When, under the same reaction conditions,
the p -methoxy-phenylimine of benzaldehyde
was reacted with butanone, a 1:1.2 mixture of diastereomers (linear/branched)
was obtained.
