[1,3]-dipolar intramolecular nitrone olefin cycloaddition reaction of a sugar-derived α,β-unsaturated ester:: a new diastereo- and regioselective synthesis of an aminocyclopentitol

被引：17

作者：

Jachak, SM ^{[1
]}

Karche, NP ^{[1
]}

Dhavale, DD ^{[1
]}

机构：

[1] Univ Pune, Garware Res Ctr, Dept Chem, Pune 411007, Maharashtra, India

来源：

TETRAHEDRON LETTERS | 2001年 / 42卷 / 29期

关键词：

nitrones; cycloadditions; cyclitols; isoxazolidines; enzyme inhibitors; glycosidation;

D O I：

10.1016/S0040-4039(01)00877-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of hemiacetal 2a, from the sugar derived alpha,beta -unsaturated ester 1a, with N-benzylhydroxylamine hydrochloride in situ generates an N-benzylnitrone as a 1,3-dipole, which spontaneously undergoes diastereo- and regioselective intramolecular nitrone olefin cycloaddition to afford a hydroxy functionalised 4-exo -ethoxycarbonyl-3-oxa-2-azabicy-clo[3.3.0]octane system, a precursor to a hitherto unknown aminocyclopentitol derivative. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：4925 / 4928

页数：4

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