Asymmetric phase-transfer alkylation catalyzed by a chiral quaternary phosphonium salt with a multiple hydrogen-bonding site

被引:95
作者
Manabe, K [1 ]
机构
[1] Univ Tokyo, Grad Sch Pharmaceut Sci, Bunkyo Ku, Tokyo 1130033, Japan
关键词
asymmetric reactions; hydrogen bonding; phase transfer; phosphonium salts;
D O I
10.1016/S0040-4039(98)01181-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A chiral phosphonium salt has been synthesized as a novel phase-transfer catalyst, and used for asymmetric benzylation of t-butyl 2-oxocyclopentanecarboxylate to give the corresponding product with up to 50% ee. (C) 1998 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5807 / 5810
页数:4
相关论文
共 20 条
[1]  
[Anonymous], 1997, PHASE TRANSFER CATAL
[2]   NICKEL-CATALYZED SYNTHESIS OF PHOSPHONIUM SALTS [J].
CASSAR, L ;
FOA, M .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1974, 74 (01) :75-78
[3]   A rational approach to catalytic enantioselective enolate alkylation using a structurally rigidified and defined chiral quaternary ammonium salt under phase transfer conditions [J].
Corey, EJ ;
Xu, F ;
Noe, MC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (50) :12414-12415
[4]  
Dehmlow E. V., 1993, Phase Transfer Catalysis
[5]   EFFICIENT CATALYTIC ASYMMETRIC ALKYLATIONS .1. ENANTIOSELECTIVE SYNTHESIS OF (+)-INDACRINONE VIA CHIRAL PHASE-TRANSFER CATALYSIS [J].
DOLLING, UH ;
DAVIS, P ;
GRABOWSKI, EJJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (02) :446-447
[6]   CHIRAL QUATERNARY BENZOPHENONE HYDRAZONIUM SALT DERIVATIVES - EFFICIENT CHIRAL CATALYSTS FOR THE ENANTIOSELECTIVE PHASE-TRANSFER ALKYLATION OF IMINES - APPLICATION TO SYNTHESIS OF CHIRAL PRIMARY AMINES [J].
EDDINE, JJ ;
CHERQAOUI, M .
TETRAHEDRON-ASYMMETRY, 1995, 6 (06) :1225-1228
[7]   NEW METHODS AND REAGENTS IN ORGANIC-SYNTHESIS .10. "TRIMETHYLSILYLDIAZOMETHANE(TMSCHN2) - A NEW, STABLE, AND SAFE REAGENT FOR THE HOMOLOGATION OF KETONES [J].
HASHIMOTO, N ;
AOYAMA, T ;
SHIOIRI, T .
TETRAHEDRON LETTERS, 1980, 21 (48) :4619-4622
[8]  
LANDINI D, 1976, SYNTHESIS-STUTTGART, P389
[9]   ASYMMETRIC ALKYLATION OF OXINDOLES - AN APPROACH TO THE TOTAL SYNTHESIS OF (-)-PHYSOSTIGMINE [J].
LEE, TBK ;
WONG, GSK .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (02) :872-875
[10]   A new class of asymmetric phase-transfer catalysts derived from Cinchona alkaloids - Application in the enantioselective synthesis of alpha-amino acids [J].
Lygo, B ;
Wainwright, PG .
TETRAHEDRON LETTERS, 1997, 38 (49) :8595-8598