Intramolecular N-acyliminium ion-olefin cyclization in the synthesis of optically pure isoquinoline derivatives: Control of stereochemistry and application to synthesis of morphine alkaloids

被引：14

作者：

Bottari, P ^{[1
]}

Endoma, MAA ^{[1
]}

Hudlicky, T ^{[1
]}

Ghiviriga, I ^{[1
]}

Abboud, KA ^{[1
]}

机构：

[1] Univ Florida, Dept Chem, Gainesville, FL 32611 USA

来源：

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS | 1999年 / 64卷 / 02期

关键词：

N-acyliminium ion; isoquinolines; stereochemistry; morphine; alkaloids; biooxidation;

D O I：

10.1135/cccc19990203

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The 3-[2-(cyclohex-1-enyl)ethyl]-[1,3]oxazoline-2,4-dione derivatives 9, 14 and 16 were subjected to hydride reduction followed by acid-catalyzed olefin-N-acyliminium ion cyclization to afford a series of perhydroisoquinolines 10, 11a, 11b, 19a-19c, 20a, 20b and 21. A mechanism was proposed that accounts for the observed stereoselectivity of the cyclization reactions based on the neighboring group participation by a benzoate group.

引用

页码：203 / 216

页数：14

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