Asymmetric cleavage of chiral alpha,beta-ethylenic acetals by organolithium reagents

被引:8
作者
Alexakis, A
Mhamdi, F
Lagasse, F
Mangeney, P
机构
[1] Lab. de Chim. des Organo-Elements, CNRS UA 473, case 183 Univ. P. et M. Curie, F-75252 Paris Cedex 05, 4, Place Jussieu
关键词
D O I
10.1016/S0957-4166(96)00438-7
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
alpha,beta-Ethylenic chiral acetals react regio- and stereoselectively with organolithium reagents. The obtained enol ether may be hydrolyzed into a chiral beta-disubstituted aldehyde. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:3343 / 3346
页数:4
相关论文
共 10 条
[1]   CHIRAL ACETALS IN ASYMMETRIC-SYNTHESIS [J].
ALEXAKIS, A ;
MANGENEY, P .
TETRAHEDRON-ASYMMETRY, 1990, 1 (08) :477-511
[2]   CHIRAL ACETALS IN ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SUBSTITUTION OR ELIMINATION-REACTIONS [J].
ALEXAKIS, A ;
MANGENEY, P ;
GHRIBI, A ;
MAREK, I ;
SEDRANI, R ;
GUIR, C ;
NORMANT, J .
PURE AND APPLIED CHEMISTRY, 1988, 60 (01) :49-56
[3]   FACILE SN' REACTION OF ALKYL-LITHIUMS WITH 2-VINYL-1,3-DIOXANE [J].
BAILEY, WF ;
ZARTUN, DL .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (01) :34-35
[4]   ACETALS AS CHIRAL AUXILIARIES .4. ASYMMETRIC-SYNTHESIS OF GAMMA,DELTA-ETHYLENIC ALDEHYDES - AN APPROACH TO THE CALIFORNIA RED SCALE PHEROMONE [J].
MANGENEY, P ;
ALEXAKIS, A ;
NORMANT, JF .
TETRAHEDRON LETTERS, 1987, 28 (21) :2363-2366
[5]  
MANGENEY P, 1986, TETRAHEDRON LETT, V27, P2143
[6]  
MANNA S, 1984, TETRAHEDRON LETT, V25, P519
[7]  
MOOL K, 1978, TETRAHEDRON LETT, P2143
[8]   NUCLEOPHILIC CLEAVAGE OF ACETALS USING ORGANOMETALLIC REAGENTS [J].
MORI, A ;
FUJIWARA, J ;
MARUOKA, K ;
YAMAMOTO, H .
JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1985, 285 (1-3) :83-94
[9]  
QUELET R, 1967, CR ACAD SCI C CHIM, V264, P1316