1,7-induction of chirality in Mukaiyama aldol reactions using π-allyltricarbonyliron lactone and lactam complexes as chiral templates

被引:15
作者
Ley, SV [1 ]
Cox, LR [1 ]
Middleton, B [1 ]
Worrall, JM [1 ]
机构
[1] Univ Cambridge, Dept Chem, Cambridge CB2 1EW, England
关键词
D O I
10.1016/S0040-4020(98)01159-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The Mukaiyama aldol reactions of silyl enol ether-substituted pi-allyltricarbonyliron lactone and lactam complexes with aldehydes under BF3. OEt2 activation proceed with moderate to excellent diastereocontrol. The level of diastereocontrol is strongly affected by the nature of the endo substituent on the complex, seven carbon atoms distant from the reaction site. A detailed investigation of the reaction is presented and a model for the observed stereoselectivity proposed. (C) 1999 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:3515 / 3530
页数:16
相关论文
共 64 条
[1]   The anti-selective boron-mediated asymmetric aldol reaction of carboxylic esters [J].
Abiko, A ;
Liu, JF ;
Masamune, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1997, 119 (10) :2586-2587
[2]   CHIRAL QUARTERNARY AMMONIUM FLUORIDE - A NEW REAGENT FOR CATALYTIC ASYMMETRIC ALDOL REACTIONS [J].
ANDO, A ;
MIURA, T ;
TATEMATSU, T ;
SHIORI, T .
TETRAHEDRON LETTERS, 1993, 34 (09) :1507-1510
[3]   STEREOSELECTIVE ALDOL REACTIONS WITH ALPHA-UNSUBSTITUTED CHIRAL ENOLATES [J].
BRAUN, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (01) :24-37
[4]  
Braun M., 1992, ADV CARBANION CHEM, V1, P177
[5]   EFFECTIVE 1,7-ASYMMETRIC INDUCTION IN REACTIONS BETWEEN 6-HYDROXYALLYLSTANNANES AND ALDEHYDES PROMOTED BY TIN(IV) BROMIDE [J].
CAREY, JS ;
THOMAS, EJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (03) :283-284
[6]   ENANTIOSELECTIVE MUKAIYAMA-ALDOL AND ALDOL-DIHYDROPYRONE ANNULATION REACTIONS CATALYZED BY A TRYPTOPHAN-DERIVED OXAZABOROLIDINE [J].
COREY, EJ ;
CYWIN, CL ;
ROPER, TD .
TETRAHEDRON LETTERS, 1992, 33 (46) :6907-6910
[7]   Chemistry of trichlorosilyl enolates .1. New reagents for catalytic, asymmetric aldol additions [J].
Denmark, SE ;
Winter, SBD ;
Su, XP ;
Wong, KT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (31) :7404-7405
[8]   Lewis base-catalyzed, asymmetric aldol additions of methyl ketone enolates [J].
Denmark, SE ;
Stavenger, RA ;
Wong, KT .
JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (04) :918-919
[9]   ENANTIOSELECTIVE SYNTHESES WITH TITANIUM-CARBOHYDRATE COMPLEXES .2. ENANTIOSELECTIVE ALDOL REACTION OF TERT-BUTYL ACETATE USING TITANIUM-CARBOHYDRATE COMPLEXES [J].
DUTHALER, RO ;
HEROLD, P ;
LOTTENBACH, W ;
OERTLE, K ;
RIEDIKER, M .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1989, 28 (04) :495-497