Direct proline catalyzed asymmetric α-aminooxylation of aldehydes

被引：296

作者：

Hayashi, Y ^{[1
]}

Yamaguchi, J ^{[1
]}

Hibino, K ^{[1
]}

Shoji, M ^{[1
]}

机构：

[1] Univ Tokyo, Fac Engn, Dept Ind Chem, Shinjuku Ku, Tokyo 1628601, Japan

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 45期

关键词：

organocatalyst; asymmetric reaction; catalytic reaction; proline; alpha-aminooxylation;

D O I：

10.1016/j.tetlet.2003.09.057

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The direct catalytic enantioselective alpha-aminooxylation of aldehydes has been developed using nitrosobenzene as the oxygen source and L-proline as catalyst, affording versatile alpha-aminooxylated aldehydes in high yield with excellent enantioselectivities. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：8293 / 8296

页数：4

共 33 条

[1] Bogevig A, 2002, ANGEW CHEM INT EDIT, V41, P1790, DOI 10.1002/1521-3773(20020517)41:10<1790::AID-ANIE1790>3.0.CO
[2] 2-Y
[3] The direct and enantioselective organocatalytic α-oxidation of aldehydes
Brown, SP
Brochu, MP
Sinz, CJ
MacMillan, DWC
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (36) : 10808 - 10809
[4] A novel chiral synthetic equivalent of glyoxal and its application to the asymmetric synthesis of O-protected α-hydroxy aldehydes
Colombo, L
Di Giacomo, M
[J]. TETRAHEDRON LETTERS, 1999, 40 (10) : 1977 - 1980
[5] A highly enantioselective route to either enantiomer of both α- and β-amino acid derivatives
Córdova, A
Watanabe, S
Tanaka, F
Notz, W
Barbas, CF
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) : 1866 - 1867
[6] LEUKOTRIENE-B - TOTAL SYNTHESIS AND ASSIGNMENT OF STEREOCHEMISTRY
COREY, EJ
MARFAT, A
GOTO, G
BRION, F
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1980, 102 (27) : 7984 - 7985
[7] Proline-catalyzed asymmetric α-amination of aldehydes and ketones -: An astonishingly simple access to optically active α-hydrazino carbonyl compounds
Duthaler, RO
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (09) : 975 - 978
[8] PREPARATION OF OPTICALLY PURE L-2-HYDROXYALDEHYDES WITH YEAST TRANSKETOLASE
EFFENBERGER, F
NULL, V
ZIEGLER, T
[J]. TETRAHEDRON LETTERS, 1992, 33 (36) : 5157 - 5160
[9] ELIEL EL, 1983, ASYMMETRIC SYNTHESIS, V2, P125
[10] Enders D, 1996, LIEBIGS ANN, P11

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