High pressure mediated asymmetric Henry reaction of nitromethane with carbonyl compounds catalyzed by cinchona alkaloids

被引:0
作者
Misumi, Y [1 ]
Bulman, RA
Matsumoto, K
机构
[1] Kyoto Univ, Grad Sch Human & Environm Studies, Kyoto 6068501, Japan
[2] Natl Radiol Protect Board, Didcot OX11 0RQ, Oxon, England
关键词
Henry reaction; asymmetric reaction; high pressure effect; nitro alcohol; cinchona alkaloid;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Asymmetric nitroaldol reactions, catalyzed by cinchona alkaloid, of nitromethane have been investigated. High pressure played an interesting role in the overall reactions that form beta-nitro alcohols. From the enantiomeric states of the products formed under different reaction conditions, we deduce that the nature of transition termolecular species formed by the carbonyl compounds with quinidine or quinine determines the stereoselective outcome of the reaction under high pressure.
引用
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页码:599 / 605
页数:7
相关论文
共 17 条
[1]   ENANTIOMERICALLY PURE GUANIDINE-CATALYZED ASYMMETRIC NITROALDOL REACTION [J].
CHINCHILLA, R ;
NAJERA, C ;
SANCHEZAGULLO, P .
TETRAHEDRON-ASYMMETRY, 1994, 5 (07) :1393-1402
[2]   SYNTHESIS AND INVESTIGATION OF A HINDERED, CHIRAL, BICYCLIC GUANIDINE [J].
DAVIS, AP ;
DEMPSEY, KJ .
TETRAHEDRON-ASYMMETRY, 1995, 6 (11) :2829-2840
[3]   Catalytic asymmetric nitroaldol reaction of alpha,alpha-difluoro aldehydes mediated by rare earth lithium BINOL complexes [J].
Iseki, K ;
Oishi, S ;
Sasai, H ;
Shibasaki, M .
TETRAHEDRON LETTERS, 1996, 37 (50) :9081-9084
[4]   High pressure and selectivity in organic reactions. [J].
Jenner, G .
TETRAHEDRON, 1997, 53 (08) :2669-2695
[5]   Catalytic enantioselective Baylis-Hillman reactions. Correlation between pressure and enantiomeric excess [J].
Marko, IE ;
Giles, PR ;
Hindley, NJ .
TETRAHEDRON, 1997, 53 (03) :1015-1024
[6]   HIGH-PRESSURE SYNTHESES - THE HENRY REACTION [J].
MATSUMOTO, K .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1984, 23 (08) :617-618
[7]   Novel synthetic approach to 1 alpha,24(R)-dihydroxyvitamin D-3 using an asymmetric nitroaldol reaction [J].
Oshida, J ;
Okamoto, M ;
Azuma, S ;
Tanaka, T .
TETRAHEDRON-ASYMMETRY, 1997, 8 (15) :2579-2584
[8]  
ROSINI G, 1988, SYNTHESIS-STUTTGART, P833
[9]  
Rosini G., 1991, COMPREHENSIVE ORGANI, V2, P321, DOI DOI 10.1016/B978-0-08-052349-1.00032-9
[10]   SYNTHESES OF (S)-(-)-PINDOLOL AND [3'-C-13]-(R)-(-)-PINDOLOL UTILIZING A LANTHANUM-TITHIUM-(R)-BINOL ((R)-LLB) CATALYZED NITROALDOL REACTION [J].
SASAI, H ;
YAMADA, YMA ;
SUZUKI, T ;
SHIBASAKI, M .
TETRAHEDRON, 1994, 50 (43) :12313-12318