A NEW SYNTHESIS OF HIGHLY FUNCTIONAL NITRONES THROUGH A NITROSOKETENE INTERMEDIATE AND THEIR USE FOR THE STEREOSELECTIVE SYNTHESIS OF AMINO-ACIDS

被引：38

作者：

KATAGIRI, N ^{[1
]}

SATO, H ^{[1
]}

KURIMOTO, A ^{[1
]}

OKADA, M ^{[1
]}

YAMADA, A ^{[1
]}

KANEKO, C ^{[1
]}

机构：

[1] TOHOKU UNIV,INST PHARMACEUT,SENDAI,MIYAGI 98077,JAPAN

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 26期

关键词：

D O I：

10.1021/jo00105a029

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Reaction of 5-isonitroso-2,2-dimethyl-1,3-dioxane-4,6-dione with various ketones under reflux in toluene gives 3-oxazolin-5-one 3-oxides (cyclic nitrones) via a nitrosoketene intermediate generated from the isonitroso derivative. The cyclic nitrones can be used for the stereoselective [3 + 2] dipolar cycloaddition to electron-rich olefins under high pressure to produce fused isoxazolidines. These isoxazolidines, in turn, are versatile intermediates for the stereoselective preparation of substituted alpha-amino acids.

引用

页码：8101 / 8106

页数：6

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