ASYMMETRIC DIELS-ALDER REACTIONS WITH ALPHA,BETA-UNSATURATED ACETALS

被引:32
作者
SAMMAKIA, T
BERLINER, MA
机构
[1] Department of Chemistry and Biochemistry, University of Colorado, Colorado 80309-0215, Boulder
关键词
D O I
10.1021/jo00102a006
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chiral alpha,beta-unsaturated acetals derived from 2,4-pentanediol are shown to undergo Lewis acid promoted Diels-Alder reactions with good diastereoselectivity.
引用
收藏
页码:6890 / 6891
页数:2
相关论文
共 21 条
[1]   CHIRAL ACETALS IN ASYMMETRIC-SYNTHESIS [J].
ALEXAKIS, A ;
MANGENEY, P .
TETRAHEDRON-ASYMMETRY, 1990, 1 (08) :477-511
[2]   CONFORMATIONAL-ANALYSIS OF CHIRAL ALKENES AND OXONIUM IONS - ABINITIO MOLECULAR-ORBITAL CALCULATIONS AND AN IMPROVED MM2 FORCE-FIELD [J].
BROEKER, JL ;
HOFFMANN, RW ;
HOUK, KN .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (13) :5006-5017
[3]   ON THE STEREOSELECTIVE OPENING OF ACHIRAL DIOXANE ACETALS [J].
DENMARK, SE ;
ALMSTEAD, NG .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (22) :6458-6467
[4]   STUDIES ON THE MECHANISM AND ORIGIN OF STEREOSELECTIVE OPENING OF CHIRAL DIOXANE ACETALS [J].
DENMARK, SE ;
ALMSTEAD, NG .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (21) :8089-8110
[5]   ON THE STEREOSELECTIVE OPENING OF CHIRAL DIOXANE ACETALS - NUCLEOPHILE DEPENDENCE [J].
DENMARK, SE ;
ALMSTEAD, NG .
JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (23) :6485-6487
[6]   ASYMMETRIC DIELS-ALDER CYCLO-ADDITION REACTIONS WITH CHIRAL ALPHA, BETA-UNSATURATED N-ACYLOXAZOLIDINONES [J].
EVANS, DA ;
CHAPMAN, KT ;
BISAHA, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (04) :1238-1256
[7]   THE LOW-TEMPERATURE, IONIC DIELS-ALDER ADDITION OF VINYL ORTHO ESTERS TO 1,3-DIENES [J].
GASSMAN, PG ;
CHAVAN, SP .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (10) :2392-2394
[8]   ETHYNYL ORTHO-ESTERS AS PRECURSORS OF PROPARGYL CATIONS - THE LOW-TEMPERATURE, IONIC DIELS-ALDER ADDITION OF ETHYL PROPIOLATE TO 1,3-DIENES VIA ETHYNYL ORTHO-ESTERS [J].
GASSMAN, PG ;
CHAVAN, SP .
TETRAHEDRON LETTERS, 1988, 29 (28) :3407-3410
[10]   ACROLEIN ACETALS AS ALLYL CATION PRECURSORS IN THE IONIC DIELS-ALDER REACTION [J].
GASSMAN, PG ;
SINGLETON, DA ;
WILWERDING, JJ ;
CHAVAN, SP .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (07) :2182-2184