Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2005(14): 2445-2448
DOI: 10.1055/s-2005-872087
DOI: 10.1055/s-2005-872087
PSP
© Georg Thieme Verlag Stuttgart · New York
Large-Scale Synthesis of Chiral Ferrocenyl Imino-Phosphines
Further Information
Received
15 June 2004
Publication Date:
20 July 2005 (online)
Publication History
Publication Date:
20 July 2005 (online)
Abstract
A convenient, multigram-scale synthesis of ferrocenyl imino-phosphine ligands, combining planar and central chirality, and featured by a flexible and easy-to-tune molecular structure has been developed.
Key words
imines - ferrocenes - phosphorus - ligands - stereoselective synthesis
-
1a
Hayashi T. In Ferrocenes: Homogeneous Catalysis, Organic Synthesis, Materials ScienceTogni A.Hayashi T. VCH; Weinheim: 1995. p.105 -
1b
Colacot TJ. Chem. Rev. 2003, 103: 3101 -
1c
Dai LX.Tu T.You SL.Deng WP.Hou XL. Acc. Chem. Res. 2003, 36: 659 -
1d
Barbaro P.Bianchini C.Giambastiani G.Parisel SL. Coord. Chem. Rev. 2004, 248: 2131 - 2
Hayashi T.Yamamoto K.Kumada M. Tetrahedron Lett. 1974, 4405 -
3a
Togni A. Angew. Chem. Int. Ed. Engl. 1996, 35: 1475 -
3b
Stinson S. C. Chem. Eng. News 1997, October 20: 38 -
3c
McGarrity J,Spindler F,Fuchs R, andEyer M. inventors; Eur. Pat. Appl. EP 624587A2. ; Chem. Abstr. 1995, 122, P81369q -
4a
Togni A. Chimia 1996, 50: 86 -
4b
Spindler F.Pugin B.Jalett HP.Buser HP.Pittelkow U.Blaser HU. In Catalysis of Organic Reactions: Chemical Industry Vol. 68:Malz RE. Dekker; New York: 1996. p.153 - For a review on 1,2-substituted P,N ligands, see:
-
5a
Richards CJ.Locke AJ. Tetrahedron: Asymmetry 1998, 9: 2377 -
5b
Togni A.Venanzi LM. Angew. Chem. Int. Ed. Engl. 1994, 33: 497 -
5c
Togni A.Bieler N.Burckhardt U.Köllner C.Pioda G.Schneider R.Schnyder A. Pure Appl. Chem. 1999, 71: 1531 -
5d
Guiry PJ.Saunders CP. Adv. Synth. Catal. 2004, 346: 497 - For recent examples of various 1,2-substituted P,C=N ferrocenyl ligands, see:
-
6a
You S.-L.Hou X.-L.Dai L.-X.Yu Y.-H.Xia W. J. Org. Chem. 2002, 67: 4684 -
6b
Burckhardt U.Drommi D.Togni A. Inorg. Chim. Acta 1999, 296: 183 -
6c
Malone YM.Guiry PJJ. Organomet. Chem. 2000, 603: 110 -
6d
Deng W.-P.Hou X.-L.Dai L.-X.Dong X.-W. Chem. Commun. 2000, 1483 -
6e
Deng W.-P.You S.-L.Hou X.-L.Dai L.-X.Yu Y.-H.Xia W.Sun J. J. Am. Chem. Soc. 2001, 123: 6508 -
6f
Takei I.Nishibayashi Y.Ishii Y.Mizobe Y.Uemura S.Hidai M. Chem. Commun. 2001, 2360 -
6g
Enders D.Peters R.Lochtman R.Raabe G.Runsink J.Bats JW. Eur. J. Org. Chem. 2000, 3399 -
7a
Hu X.Dai H.Hu X.Chen H.Wang J.Bai C.Zheng Z. Tetrahedron: Asymmetry 2002, 13: 1687 -
7b
Hayashi T.Hayashi C.Uozumi Y. Tetrahedron: Asymmetry 1995, 6: 2503 -
7c
Tu T.Zhou Y.-G.Hou X.-L.Dai L.-X.Dong X.-C.Yu Y.-H.Sun J. Organometallics 2003, 22: 1255 -
7d
Hu X.Chen H.Hu X.Dai H.Bai C.Wang J.Zheng Z. Tetrahedron Lett. 2002, 43: 9179 -
7e
Park H.-J.Han JW.Seo H.Jang HY.Chung YK.Suh J. J. Mol. Catal. A: Chem. 2001, 174: 151 -
7f
Hu X.Dai H.Bai C.Chen H.Zheng Z. Tetrahedron: Asymmetry 2004, 15: 1065 -
8a
Lotz M.Ireland T.Tappe K.Knochel P. Chirality 2000, 12: 389 -
8b
Kloetzing RJ.Lotz M.Knochel P. Tetrahedron: Asymmetry 2003, 14: 255 - 9
Barbaro P.Bianchini C.Giambastiani G.Togni A. Tetrahedron Lett. 2003, 44: 8279 -
10a
Köllner C.Pugin B.Togni A. J. Am. Chem. Soc. 1998, 120: 10274 -
10b
Schneider R.Köllner C.Weber I.Togni A. Chem. Commun. 1999, 2415 -
10c
CIBA-GEIGY AG. inventors; WO 96/32400. -
11a
Hayashi T.Mise T.Fukushima M.Kagotani M.Nagashima N.Hamada Y.Matsumoto A.Kawakami S.Konishi M.Yamamoto K.Kumada M. Bull. Chem. Soc. Jpn. 1980, 53: 1138 -
11b
Gokel GW.Marquarding D.Ugi IK. J. Org. Chem. 1972, 37: 3052 -
11c
Togni A.Breutel C.Schnyder A.Spindler F.Landert H.Tijani A. J. Am. Chem. Soc. 1994, 116: 4062