Catalytic asymmetric nitroaldol reaction of alpha,alpha-difluoro aldehydes mediated by rare earth lithium BINOL complexes

被引：64

作者：

Iseki, K ^{[1
]}

Oishi, S ^{[1
]}

Sasai, H ^{[1
]}

Shibasaki, M ^{[1
]}

机构：

[1] UNIV TOKYO,FAC PHARMACEUT SCI,BUNKYO KU,TOKYO 113,JAPAN

来源：

TETRAHEDRON LETTERS | 1996年 / 37卷 / 50期

关键词：

D O I：

10.1016/S0040-4039(96)02090-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Rare earth-Li-BINOL complexes were used to catalyze nitroaldol reactions of alpha,alpha-difluoro aldehydes with nitromethane in a good enantioselective manner. The optical yields of nitroaldol 2a depend on the size of rare earth metals, and an Sm-Li-BINOL complex gave the highest enantioselectivity. The enantiotopic face selection of alpha,alpha-difluoro aldehyde 1a was found to be different from that of nonfluorinated aldehydes employed in the usual catalytic asymmetric nitroaldol reactions. Copyright (C) 1996 Elsevier Science Ltd

引用

页码：9081 / 9084

页数：4

共 36 条

[1] A new multifunctional heterobimetallic asymmetric catalyst for Michael additions and tandem Michael-Aldol reactions [J].

Arai, T ;

Sasai, H ;

Aoe, K ;

Okamura, K ;

Date, T ;

Shibasaki, M .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (01) :104-106

[2] Catalytic asymmetric synthesis of alpha-hydroxy phosphonates using the Al-Li-BINOL complex [J].

Arai, T ;

Bougauchi, M ;

Sasai, H ;

Shibasaki, M .

JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (09) :2926-2927

[3]

BRAUN M, 1995, LIEBIGS ANN, P1447

[4] PREPARATION AND PROPERTIES OF CHIRAL FLUOROORGANIC COMPOUNDS [J].

BRAVO, P ;

RESNATI, G .

TETRAHEDRON-ASYMMETRY, 1990, 1 (10) :661-692

[5] MICROWAVE SPECTRAL STUDY OF 2-FLUOROPHENOL - CIS-CONFORMER [J].

DUTTA, A ;

JAMAN, AI ;

NANDI, RN .

JOURNAL OF MOLECULAR SPECTROSCOPY, 1985, 114 (02) :274-279

[6]

Filler R., 1993, ORGANOFLUORINE COMPO

[7]

Filler R., 1982, BIOMEDICAL ASPECTS F

[8] FLUORO KETONE INHIBITORS OF HYDROLYTIC ENZYMES [J].

GELB, MH ;

SVAREN, JP ;

ABELES, RH .

BIOCHEMISTRY, 1985, 24 (08) :1813-1817

[9] FLUORO KETONE PHOSPHOLIPID ANALOGS - NEW INHIBITORS OF PHOSPHOLIPASE-A2 [J].

GELB, MH .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (11) :3146-3147

[10]

Hanessian S., 1983, Total Synthesis of Natural Products: The Chiron Approach

← 1 2 3 4 →