-
1
-
-
0003445429
-
-
E. N. Jacobsen, A. Flats and H. Yamamoto, Springer, Berlin
-
J. M. Brown, in Comprehensive Asymmetric Catalysis, ed., E. N. Jacobsen, A. Flats, and, H. Yamamoto, Springer, Berlin, 1999
-
(1999)
Comprehensive Asymmetric Catalysis, Ed.
-
-
Brown In, J.M.1
-
2
-
-
0003544583
-
-
I. Ojima, Wiley-VCH, New York, 2nd edn
-
T. Ohkuma, M. Kitamura and R. Noyori, in Catalytic Asymmetric Synthesis, ed., I. Ojima, Wiley-VCH, New York, 2nd edn, 2000
-
(2000)
Catalytic Asymmetric Synthesis, Ed.
-
-
Ohkuma, T.1
Kitamura, M.2
Noyori In, R.3
-
5
-
-
0034697497
-
-
H.-U. Blaser and E. Schmidt, Wiley-VCH, Weinheim
-
Asymmetric Catalysis on Industrial Scale, ed., H.-U. Blaser, and, E. Schmidt, Wiley-VCH, Weinheim, 2004
-
(2004)
Asymmetric Catalysis on Industrial Scale, Ed.
-
-
-
17
-
-
31944450636
-
-
While organocatalysis has developed at a rapid pace only recently, its origins stretch back to the beginning of the previous century. For selected early examples of asymmetric organocatalysis see:
-
S. Bell B. Wüstenberg S. Kaiser F. Menges T. Netscher A. Pfaltz Science 2006 311 642
-
(2006)
Science
, vol.311
, pp. 642
-
-
Bell, S.1
Wüstenberg, B.2
Kaiser, S.3
Menges, F.4
Netscher, T.5
Pfaltz, A.6
-
20
-
-
33745931185
-
-
R. Wegler Ann. 1932 498 62
-
(1932)
Ann.
, vol.498
, pp. 62
-
-
Wegler, R.1
-
25
-
-
34250645639
-
-
K. Mikami and M. Lautens, Wiley, Hoboken
-
Recent reviews: G. Lelais, D. W. C. MacMillan, in Frontiers in Asymmetric Catalysis, ed., K. Mikami, and, M. Lautens, Wiley, Hoboken, 2007
-
(2007)
Frontiers in Asymmetric Catalysis, Ed.
-
-
Lelais, G.1
MacMillan In, D.W.C.2
-
44
-
-
0003717374
-
-
Freeman, New York, 5th edn
-
J. M. Berg, J. L. Tymoczko, L. Stryer, Biochemistry, Freeman, New York, 5th edn, 2002
-
(2002)
Biochemistry
-
-
Berg, J.M.1
Tymoczko, J.L.2
Stryer, L.3
-
45
-
-
33947466443
-
-
Karrer and co-workers had earlier shown that 1,4-dihydropyridines could reduce methylene blue, however, proof of direct hydrogen transfer could not be obtained (via deuterium labelling experiments) due to the likelihood of fast exchange of the transferred H/D in the product with the solvent.
-
D. Mauzerall F. H. Westheimer J. Am. Chem. Soc. 1955 77 2261
-
(1955)
J. Am. Chem. Soc.
, vol.77
, pp. 2261
-
-
Mauzerall, D.1
Westheimer, F.H.2
-
47
-
-
84965040591
-
-
For a later study demonstrating the reduction of other keto acids see:
-
A. Hantzsch Justus Liebigs Ann. Chem. 1882 215 1
-
(1882)
Justus Liebigs Ann. Chem.
, vol.215
, pp. 1
-
-
Hantzsch, A.1
-
65
-
-
0003607021
-
-
A. R. Katritzky, C. W. Rees and E. F. V. Scriven, Pergamon, Oxford, p. 135
-
M. Lounasmaa, A. Tolvanen, in Comprehensive Heterocyclic Chemistry II, ed., A. R. Katritzky, C. W. Rees, and, E. F. V. Scriven, Pergamon, Oxford, 1996, vol. 5, p. 135
-
(1996)
Comprehensive Heterocyclic Chemistry II, Ed.
-
-
Lounasmaa, M.1
Tolvanen In, A.2
-
116
-
-
33845377781
-
-
A. G. Talma P. Jouin J. G. de Vries C. B. Troostwijk G. H. Werumeus Buning J. K. Waninge J. Visscher R. M. Kellogg J. Am. Chem. Soc. 1985 107 3981
-
(1985)
J. Am. Chem. Soc.
, vol.107
, pp. 3981
-
-
Talma, A.G.1
Jouin, P.2
De Vries, J.G.3
Troostwijk, C.B.4
Werumeus Buning, G.H.5
Waninge, J.K.6
Visscher, J.7
Kellogg, R.M.8
-
128
-
-
33744723131
-
-
For a recent example of a chiral metal-based catalyst promoting enantioselective reductions of α-keto esters using stoichiometric loadings of a Hanztsch dihydropyridine see:
-
R. Saito S. Naruse K. Takano K. Fukuda A. Katoh Y. Inoue Org. Lett. 2006 8 2067
-
(2006)
Org. Lett.
, vol.8
, pp. 2067
-
-
Saito, R.1
Naruse, S.2
Takano, K.3
Fukuda, K.4
Katoh, A.5
Inoue, Y.6
-
142
-
-
33847086871
-
-
For a review concerning recent developments in both metal-free and metal-assisted Brønsted acid catalysts see:
-
W. P. Jencks Acc. Chem. Res. 1980 13 161
-
(1980)
Acc. Chem. Res.
, vol.13
, pp. 161
-
-
Jencks, W.P.1
-
144
-
-
0003554758
-
-
For reports concerning the reduction of imines/reductive amination of aldehydes/ketones using achiral thiourea catalysts see:
-
M. S. Sigman E. N. Jacobsen J. Am. Chem. Soc. 1998 120 4901
-
(1998)
J. Am. Chem. Soc.
, vol.120
, pp. 4901
-
-
Sigman, M.S.1
Jacobsen, E.N.2
-
149
-
-
30744457769
-
-
The authors use optical rotation data to determine levels of enantiomeric excess and cite previous work by Kagan et al., curiously the absolute configuration of 36 is not given by Singh even though it was determined by Kagan. We have assumed that Singh used the same conditions as Kagan in assigning the absolute configuration of 36:
-
S. Singh U. K. Batra Ind. J. Chem. 1989 28B 1
-
(1989)
Ind. J. Chem.
, vol.28
, pp. 1
-
-
Singh, S.1
Batra, U.K.2
-
152
-
-
2342521907
-
-
For a short monograph concerning the use of chiral phosphoric acids as catalysts for enantioselective addition reactions to imines see:
-
D. Uraguchi M. Terada J. Am. Chem. Soc. 2004 126 5356
-
(2004)
J. Am. Chem. Soc.
, vol.126
, pp. 5356
-
-
Uraguchi, D.1
Terada, M.2
-
154
-
-
0004231121
-
-
John Wiley & Sons, New York, For a review detailing the use of phosphoric acid catalysts in other asymmetric transformations see ref. 6i
-
a of diethyl phosphate is 1.39: L. D. Quin, A Guide to Organophosphorus Chemistry, John Wiley & Sons, New York, 2000, ch. 5
-
(2000)
A Guide to Organophosphorus Chemistry
-
-
Quin, L.D.1
-
160
-
-
34248524344
-
-
For a previous example where VAPOL-derived phosphoric acids proved superior to BINOL-based materials see:
-
G. Li Y. Liang J. C. Antilla J. Am. Chem. Soc. 2007 129 5830
-
(2007)
J. Am. Chem. Soc.
, vol.129
, pp. 5830
-
-
Li, G.1
Liang, Y.2
Antilla, J.C.3
-
172
-
-
27544485685
-
-
The authors point out that combining asymmetric processes results in a mathematical requirement for an improvement in enantioselectivity. For example, if two catalytic cycles are combined, both of which give products with 86% ee, the cascade will give a 7: 1 mixture of diastereomers and the major diastereomer will be formed in 99% ee
-
Y. Huang A. M. Walji C. H. Larsen D. W. C. MacMillan J. Am. Chem. Soc. 2006 127 15051
-
(2006)
J. Am. Chem. Soc.
, vol.127
, pp. 15051
-
-
Huang, Y.1
Walji, A.M.2
Larsen, C.H.3
MacMillan, D.W.C.4
-
176
-
-
34447301519
-
-
For a second report detailing a (S)-proline catalysed domino process involving a reduction reaction that does not generate enantioenriched products see:
-
D. B. Ramachary M. Kishor J. Org. Chem. 2007 72 5056
-
(2007)
J. Org. Chem.
, vol.72
, pp. 5056
-
-
Ramachary, D.B.1
Kishor, M.2
-
182
-
-
33947668980
-
-
For a similar strategy in a photoinduced dihydropyridine-mediated reduction of chalcone oxides not under the influence of catalysis see:
-
B. Procuranti S. J. Connon Chem. Commun. 2007 1421
-
(2007)
Chem. Commun.
, pp. 1421
-
-
Procuranti, B.1
Connon, S.J.2
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