Sequential One-Pot Isomerization-Wittig Olefination-Hydrogenation

被引：4
|
作者：
Sabitha, Gowravaram [1 ]
Nayak, Sambit [1 ]
Bhikshapathi, M. [1 ]
Chittapragada, Maruthi [1 ]
Yadav, J. S. [1 ,2 ]
机构：
[1] Indian Inst Chem Technol, Div Organ Chem, Hyderabad 500607, Andhra Pradesh, India
[2] King Saud Univ, Bee Res Chair, Coll Food & Agr Sci, Riyadh, Saudi Arabia
来源：
SYNTHESIS-STUTTGART | 2011年 / 22期
关键词：
isomerization; Wittig olefination; hydrogenation; oxa-Michael reaction; aldehydes; CONFIGURATION; MACROLIDE;
D O I：
10.1055/s-0030-1260232
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Primary allylic alcohols are isomerized to aldehydes in the presence of Pd(OH)(2) and homologated to alpha,beta-unsaturated carbonyl derivatives in one-pot by addition of stabilized Wittig ylides in a sequential fashion. When the reaction was prolonged by addition of more catalyst, a hydrogenation step succeeds the Wittig olefination. In addition, sequential isomerization-Wittig olefination-oxa-Michael addition reaction provides tetrahydropyran with high diastereoselectivity.
引用
收藏
页码：3661 / 3668
页数：8
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