Abstract
Ethylene and propylene carbonates are shown to be alternative
polar aprotic solvents for cross-aldol reactions catalysed by the
primary amino acids (S )-phenylalanine
and (S )-tryptophan. In contrast to the
corresponding proline-catalysed reactions, both enantiomers of these
naturally occurring, primary amino acids are available at low cost.
The optimal catalyst and solvent combination needs to be determined
on a substrate by substrate basis.
Key words
aldol reaction - amino acids - asymmetric catalysis - green chemistry - cyclic carbonate
References
1a
Pellissier H.
Tetrahedron
2007,
63:
9267
1b
Gaunt MJ.
Johansson CCC.
McNally A.
Vo NT.
Drug Discovery
Today
2007,
12:
8
1c
Dondoni A.
Massi A.
Angew. Chem. Int. Ed.
2008,
47:
4638
1d
Melchiorre P.
Marigo M.
Carlone A.
Bartoli G.
Angew. Chem. Int. Ed.
2008,
47:
6138
1e
Pellissier H.
Recent Developments in Asymmetric Organocatalysis
RSC
Publishing;
Cambridge:
2010.
2a
List B.
Synlett
2001,
1675
2b
Gröger H.
Wilken J.
Angew. Chem.
Int. Ed.
2001,
40:
529
2c
List B.
Tetrahedron
2002,
58:
5573
2d
Jarvo ER.
Miller SJ.
Tetrahedron
2002,
58:
2481
2e
List B.
Acc.
Chem. Res.
2004,
37:
548
2f
Kazmaier U.
Angew.
Chem. Int. Ed.
2005,
44:
2186
Proline is also widely used as a
chiral reagent and chiral auxiliary. For examples, see:
3a
Belokon YN.
Bulychev AG.
Vitt SV.
Struchkov YT.
Batsanov AS.
Timofeeva TV.
Tsyryapkin VA.
Ryzhov MG.
Lysova LA.
Bakhmutov VI.
Belikov VM.
J. Am. Chem. Soc.
1985,
107:
4252
3b
North M.
Zagotto G.
Synlett
1995,
639
3c
Albers T.
Biagini SCG.
Hibbs DE.
Hursthouse MB.
Malik KMA.
North M.
Uriarte E.
Zagotto G.
Synthesis
1996,
393
4 The current UK Aldrich catalogue price
for (S )-proline is £ 0.31/g
whilst the cost of (R )-proline is £ 13.32/g
(prices based on the largest available quantities). In contrast,
the
S -enantiomers of phenylalanine
and tryptophan are available for £ 0.28/g and £ 0.54/g,
respectively and the R -enantiomers are
available for £ 2.53/g and £ 2.11/g,
respectively. Thus, (R )-proline is 43
times more expensive than (S )-proline, whereas
(R )-phenylalanine is only 9 times as
expensive as (S )-phenylalanine and (R )-tryptophan is only 4 times as expensive
as (S )-tryptophan.
5
Constable DJC.
Dunn PJ.
Hayler JD.
Humphrey GR.
Leazer JL.
Linderman RJ.
Lorenz K.
Manley J.
Pearlman BA.
Wells A.
Zaksh A.
Zhang TY.
Green Chem.
2007,
9:
411
6a
Rodríguez B.
Rantanen T.
Bolm C.
Angew. Chem. Int. Ed.
2006,
46:
6924
6b
Rodríguez B.
Bruckmann A.
Bolm C.
Chem. Eur. J.
2007,
13:
4710
7a
Brogan AP.
Dickerson TJ.
Janda KD.
Angew. Chem.
Int. Ed.
2006,
45:
8100
7b
Gruttadauria M.
Giacalone F.
Noto R.
Adv.
Synth. Catal.
2009,
351:
33
8
Toma Š.
Mečiarova M.
Šebesta R.
Eur. J. Org. Chem.
2009,
321
9a
Blackmond DG.
Armstrong A.
Coombe V.
Wells A.
Angew.
Chem. Int. Ed.
2007,
46:
3798
9b
Wu B.
Liu W.
Zhang Y.
Wang H.
Chem. Eur. J.
2009,
15:
1804
10
Zotova N.
Franzke A.
Armstrong A.
Blackmond DG.
J. Am. Chem. Soc.
2007,
129:
15100
11a
North M.
Pizzato F.
Villuendas P.
ChemSusChem
2009,
2:
862
11b
Clegg W.
Harrington RW.
North M.
Pizzato F.
Villuendas P.
Tetrahedron:
Asymmetry
2010,
21:
1262
11c
North M.
Villuendas P.
Org. Lett.
2010,
12:
2378
12
Schäffner B.
Schäffner F.
Verevkin SP.
Börner A.
Chem.
Rev.
2010,
110:
4554
13a
North M.
Omedes-Pujol M.
Tetrahedron
Lett.
2009,
50:
4452
13b
North M.
Omedes-Pujol M.
Belstein J. Org. Chem.
2010,
6:
1043
14
Clements JH.
Ind.
Eng. Chem. Res.
2003,
42:
663
15
Silva LB.
Freitas LCG.
J. Mol.
Struct.: THEOCHEM
2007,
806:
23
16a
Yoshida M.
Ihara M.
Chem.
Eur. J.
2004,
10:
2886
16b
Dai W.-L.
Luo S.-L.
Yin S.-F.
Au C.-T.
Appl. Catal., A
2009,
366:
2
16c
Sakakura T.
Kohno K.
Chem. Commun.
2009,
1312
16d
North M.
Pasquale R.
Young C.
Green
Chem.
2010,
12:
1514
16e
Ballivet-Tkatchenko D.
Dibenedetto A.
Synthesis of Linear and Cyclic Carbonates , In Carbon Dioxide as Chemical Feedstock
Aresta M.
Wiley-VCH;
Weinheim:
2010.
p.169-212
17a
Meléndez J.
North M.
Pasquale R.
Eur. J. Inorg. Chem.
2007,
3323
17b
Meléndez J.
North M.
Pasquale R.
Angew. Chem. Int. Ed.
2009,
48:
2946
17c
Meléndez J.
North M.
Villuendas P.
Chem. Commun.
2009,
2577
17d
Clegg W.
Harrington RW.
North M.
Pasquale R.
Chem. Eur. J.
2010,
16:
6828
18
North M.
Villuendas P.
Young C.
Chem.
Eur. J.
2009,
11454
19
Meléndez J.
North M.
Villuendas P.
Young C.
Dalton Trans.
2011,
40:
3885
20
Metcalfe IS.
North M.
Pasquale R.
Thursfield A.
Energy Environ. Sci.
2010,
3:
212
21a
Bassan A.
Zou W.
Reyes E.
Himo F.
Córdova A.
Angew. Chem. Int. Ed.
2005,
44:
7028
21b
Córdova A.
Zou W.
Ibrahem I.
Reyes E.
Engqvist M.
Liao W.-W.
Chem. Commun.
2005,
3586
21c
Amedjkouh M.
Tetrahedron:
Asymmetry
2005,
16:
1411
21d
Dziedzic P.
Zou W.
Ibrahem I.
Sundén H.
Córdova A.
Tetrahedron Lett.
2006,
47:
6657
21e
Ramasastry SSV.
Zhang H.
Tanaka F.
Barbas CF.
J.
Am. Chem. Soc.
2007,
129:
288
21f
Utsumi N.
Imai M.
Tanaka F.
Ramasastry SSV.
Barbas CF.
Org. Lett.
2007,
9:
3445
21g
Deng D.-S.
Cai J.
Helv. Chim. Acta
2007,
90:
114
21h
Nozière B.
Córdova A.
J.
Phys. Chem. A
2008,
112:
2827
21i
Markert M.
Scheffler U.
Mahrwald R.
J.
Am. Chem. Soc.
2009,
131:
16642
21j
Chen A.
Xu J.
Chiang W.
Chai CLL.
Tetrahedron
2010,
66:
1489
22a
Jiang Z.
Liang Z.
Wu X.
Lu Y.
Chem. Commun.
2006,
2801
22b
Amedjkouh M.
Tetrahedron:
Asymmetry
2007,
18:
390
22c
Jiang Z.
Yang H.
Han X.
Luo J.
Wong MW.
Lu Y.
Org. Biomol. Chem.
2010,
8:
1368
23a
Zhang D.
Yuan C.
Tetrahedron
2008,
64:
2480
23b
Ramachary DB.
Sakthidevi R.
Chem.
Eur. J.
2009,
15:
4516
24
Billimora JD.
J.
Chem. Soc.
1955,
1126