Highly stereoselective coupling reaction of acrolein or vinyl ketone with aldehydes

被引:56
作者
Uehira, S [1 ]
Han, ZF [1 ]
Shinokubo, H [1 ]
Oshima, K [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Sakyo Ku, Kyoto 6068501, Japan
关键词
D O I
10.1021/ol990934w
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] Treatment of acrolein with a TiCL4-n-Bu(4)Nl mixed reagent in the presence of 2 equiv of aldehydes provided 4-hydroxy-1,3-dioxane derivatives in good yields with high stereoselectivities. The use of vinyl ketones instead of acrolein afforded aldo-type adducts with high syn selectivities.
引用
收藏
页码:1383 / 1385
页数:3
相关论文
共 25 条
[1]   ORGANOCOPPER REAGENTS FOR THE SYNTHESIS OF SATURATED, AND ALPHA,BETA-ETHYLENIC ALDEHYDES AND KETONES [J].
ALEXAKIS, A ;
CHUIT, C ;
COMMERCONBOURGAIN, M ;
FOULON, JP ;
JABRI, N ;
MANGENEY, P ;
NORMANT, JF .
PURE AND APPLIED CHEMISTRY, 1984, 56 (01) :91-98
[2]  
Anh N.T., 1980, TOP CURR CHEM, V88, P145
[3]  
Boons GJ, 1996, SYNLETT, P536
[4]  
Caputo R, 1991, COMPREHENSIVE ORGANI, P139
[5]  
CHEREST M, 1968, TETRAHEDRON LETT, P2199
[6]   General synthesis of alpha-acetoxy ethers from esters by DIBALH reduction and acetylation [J].
Dahanukar, VH ;
Rychnovsky, SD .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (23) :8317-8320
[7]   HYDROSILYLATION ALLYLATION SEQUENCE FOR THE STEREOSELECTIVE ELABORATION OF BETA-HYDROXY ESTERS [J].
DAVIS, AP ;
HEGARTY, SC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (07) :2745-2746
[8]  
HULCE M, 1991, COMPREHENSIVE ORGANI, V4, P237
[9]   ALDOL REACTION OF ALUMINUM ENOLATE RESULTING FROM 1,4-ADDITION OF R2ALX TO ALPHA,BETA-UNSATURATED CARBONYL COMPOUND - A 1-ACYLETHENYL ANION EQUIVALENT [J].
ITOH, A ;
OZAWA, S ;
OSHIMA, K ;
NOZAKI, H .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1981, 54 (01) :274-278
[10]  
Lee V. J., 1991, COMPREHENSIVE ORGANI, V4, P69