A tandem epoxidation/stereoselective intramolecular [4+3] cycloaddition reaction involving nitrogen-stabilized oxyallyl cations derived from chiral allenamides

被引：67

作者：

Rameshkumar, C ^{[1
]}

Hsung, RP ^{[1
]}

机构：

[1] Univ Minnesota, Dept Chem, Minneapolis, MN 55455 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2004年 / 43卷 / 05期

关键词：

chiral allenamides; cycloaddition; epoxidation; nitrogen; stereoselectivity;

D O I：

10.1002/anie.200352632

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Tandem cycling: Nitrogen-stabilized chiral oxyallyl cation intermediates are generated by chemoselective epoxidation of allenamides tethered to either the α or γ carbon atom of dienes. The stereoselectivity of the subsequent [4+3] cycloaddition step of the tandem reaction shown in the scheme depends on the length of the tether and the chiral auxiliary (N*) on the allenamide. DMDO = dimethyl dioxirane, PG = protecting group.

引用

页码：615 / 618

页数：4

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