Intramolecular ring cleavage of chiral terpenoid-derived oxazinone via asymmetric anti-aldol reaction: Unexpected entry to a N-substituted tetrahydro-1,3-oxazine-2,4-dione derivative

被引：20

作者：

Abbas, TR

Cadogan, JIG

Doyle, AA

Gosney, I

Hodgson, PKG

Howells, GE

Hulme, AN

Parsons, S

Sadler, IH

机构：

[1] UNIV LONDON IMPERIAL COLL SCI TECHNOL & MED,DEPT CHEM,LONDON SW7 2AY,ENGLAND

[2] BP CHEM LTD,RES LAB,SUNBURY TW16 7LN,MIDDX,ENGLAND

来源：

TETRAHEDRON LETTERS | 1997年 / 38卷 / 27期

关键词：

D O I：

10.1016/S0040-4039(97)01058-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

In the presence of excess Bu2BOTf to promote anti-selectivity, an asymmetric aldol reaction with a homochiral terpenoid-derived 1,3-oxazin-2-one as the chiral control element results unexpectedly in ring cleavage by an intramolecular process to form a N-substituted tetrahydro-1,3-oxazine-2,4-dione in virtually quantitative yield. (C) 1997 Elsevier Science Ltd.

引用

页码：4917 / 4920

页数：4

共 8 条

[1]

ANH HK, 1992, J ORG CHEM, V52, P5065

[2] HIGHLY REGIO-SPECIFIC AND STEREO-SPECIFIC PREPARATION OF A NEW CARBOHYDRATE-BASED 1,3-OXAZIN-2-ONE BY THE INIR METHOD AND ITS APPLICATIONS IN SOME ASYMMETRIC TRANSFORMATIONS [J].