Diastereoselective protonation of lactam enolates derived from (R)-phenylglycinol.: A novel asymmetric route to 4-phenyl-1,2,3,4-tetrahydroisoquinolines

被引：28

作者：

Philippe, N ^{[1
]}

Levacher, V ^{[1
]}

Dupas, G ^{[1
]}

Quéguiner, G ^{[1
]}

Bourguignon, J ^{[1
]}

机构：

[1] INSA, IRCOF, UPRES A 6014, Lab Chim Organ Fine & Heterocycl, F-76131 Mt St Aignan, France

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 15期

关键词：

D O I：

10.1021/ol0057939

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Highly diastereoselective protonation of chiral lactam enolates of 4-substituted-7,4-dihydroisoquinolin-3-ones is reported. Protonation and alkylation processes of these lactam enolates derived from phenylglycinol occur with opposite diastereofacial selectivity, This diastereoselective protonation has been applied to the asymmetric synthesis of (4S)-N-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline 9 obtained in up to 97% ee.

引用

页码：2185 / 2187

页数：3

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