First asymmetric synthesis of quinoline derivatives by inverse electron demand (IED) Diels-Alder reaction using chiral Ti(IV) complex

被引：149

作者：

Sundararajan, G ^{[1
]}

Prabagaran, N

Varghese, B

机构：

[1] Indian Inst Technol, Dept Chem, Madras 600036, Tamil Nadu, India

[2] Indian Inst Technol, Reg Sophisticated Instrumentat Ctr, Madras 600036, Tamil Nadu, India

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 13期

关键词：

D O I：

10.1021/ol0159221

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(matrix presented) R1, R2 = (-OCH2CH2-), (-OCH2CH2CH2-), (-CH=CH-CH2-), (-OCH2CH3, H) (R,R)-3-Aza-3-benzyl-1,5-dihydroxy-1,5-diphenylpentane (1) ligated Ti(IV) complex (1-TiCl2) is used as a chiral Lewis acid catalyst for promoting asymmetric IED Diels-Alder reaction between electron-rich dienophiles and electron-poor dienes. Here we introduce a facile route for the synthesis of asymmetric tetrahydroquinoline derivatives using the above-mentioned chiral catalyst reagent in the presence of 4 Å molecular sieves. The reactions proceed with moderate yields and at times high enantioselectivty.

引用

页码：1973 / 1976

页数：4