Diastereoselective preparation of novel tetrahydrooxazinones via heterocycloaddition of N-Boc, O-Me-acetals

被引：33

作者：

Gizecki, P ^{[1
]}

Youcef, RA ^{[1
]}

Poulard, C ^{[1
]}

Dhal, R ^{[1
]}

Dujardin, G ^{[1
]}

机构：

[1] Univ Maine, Univ Chim Organ Mol & Macromol, CNRS, UMR 6011, F-72085 Le Mans 9, France

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 52期

关键词：

oxazinones; N; O-acetals; asymmetric synthesis; pantolactone; chiral vinyl ether;

D O I：

10.1016/j.tetlet.2004.10.154

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Under Lewis acid conditions, reaction of N-Boc, O-Me acetals with the (R)-(+)-O-vinyl-pantolactone does not lead to the expected dihydrooxazine, but to the corresponding tetrahydrooxazinone, as a result of the loss of the t-Bu group. A diastereoselective and asymmetrical way to these new heterocyclic compounds is described, together with the first evidence of their ability to undergo N-acylation. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：9589 / 9592

页数：4

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