Syntheses of 2,5-disubstituted dihydrofurans from γ-substituted chiral allenamides

被引：43

作者：

Berry, CR ^{[1
]}

Hsung, RP ^{[1
]}

Antoline, JE ^{[1
]}

Petersen, ME ^{[1
]}

Challeppan, R ^{[1
]}

Nielson, JA ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2005年 / 70卷 / 10期

关键词：

D O I：

10.1021/jo0503411

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Details of a synthesis of dihydrofurans using gamma-substituted chiral allenamides are described here. Some transformations of these dihydrofurans are also examined including a highly stereoselective dihydroxylation and a rare account of a Lewis acid-mediated removal of an N-acyl substituent at the anomeric carbon of a tetrahydrofuran ring system. These studies provide further support for the synthetic utility of allenamides.

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页码：4038 / 4042

页数：5

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