Direct proline catalyzed asymmetric α-aminooxylation of aldehydes

被引:298
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
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
收藏
页码:8293 / 8296
页数:4
相关论文
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 [J].
Brown, SP ;
Brochu, MP ;
Sinz, CJ ;
MacMillan, DWC .
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 [J].
Colombo, L ;
Di Giacomo, M .
TETRAHEDRON LETTERS, 1999, 40 (10) :1977-1980
[5]   A highly enantioselective route to either enantiomer of both α- and β-amino acid derivatives [J].
Córdova, A ;
Watanabe, S ;
Tanaka, F ;
Notz, W ;
Barbas, CF .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (09) :1866-1867
[6]   LEUKOTRIENE-B - TOTAL SYNTHESIS AND ASSIGNMENT OF STEREOCHEMISTRY [J].
COREY, EJ ;
MARFAT, A ;
GOTO, G ;
BRION, F .
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 [J].
Duthaler, RO .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (09) :975-978
[8]   PREPARATION OF OPTICALLY PURE L-2-HYDROXYALDEHYDES WITH YEAST TRANSKETOLASE [J].
EFFENBERGER, F ;
NULL, V ;
ZIEGLER, T .
TETRAHEDRON LETTERS, 1992, 33 (36) :5157-5160
[9]  
ELIEL EL, 1983, ASYMMETRIC SYNTHESIS, V2, P125
[10]  
Enders D, 1996, LIEBIGS ANN, P11