Nucleophilic addition of triethyl phosphite to acetates of the Baylis-Hillman adducts: Stereoselective synthesis of (E)- and (Z)-allylphosphonates

被引:43
作者
Basavaiah, D
Pandiaraju, S
机构
[1] School of Chemistry, University of Hyderabad
关键词
D O I
10.1016/0040-4020(95)01055-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Nucleophilic addition of triethyl phosphite to 3-acetoxy-2-methylenealkanenitriles and methyl 3-acetoxy-2-methylenealkanoates provides (2E)-2-(diethoxyphosphorylmethyl)alk-2-enenitriles and methyl (2Z)-2-(diethoxyphosphorylmethyl) alk-2-enoates respectively with good stereoselectivity.
引用
收藏
页码:2261 / 2268
页数:8
相关论文
共 16 条
[11]   SYNTHETIC POTENTIAL OF THE TERTIARY-AMINE-CATALYSED REACTION OF ACTIVATED VINYL CARBANIONS WITH ALDEHYDES [J].
DREWES, SE ;
ROOS, GHP .
TETRAHEDRON, 1988, 44 (15) :4653-4670
[12]   THE BAYLIS-HILLMAN REACTION-MECHANISM AND APPLICATIONS REVISITED [J].
FORT, Y ;
BERTHE, MC ;
CAUBERE, P .
TETRAHEDRON, 1992, 48 (31) :6371-6384
[13]   DABCO-CATALYZED COUPLING OF ALDEHYDES WITH ACTIVATED DOUBLE-BONDS .1. PREPARATION OF 2-(1-HYDROXYALKYL)ACRYLIC ESTERS - SIMPLE 3-STEP SYNTHESIS OF MIKANECIC ACID [J].
HOFFMANN, HMR ;
RABE, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1983, 22 (10) :795-796
[15]  
JANECKI T, 1990, SYNTHESIS-STUTTGART, P799
[16]  
CHEM SOC REV