N-Boc-2-acyl oxazolidine methodology combined with ring-closing metathesis:: a new approach towards the enantioselective synthesis of α-(1-hydroxyalkyl) nitrogen heterocycles

被引：36

作者：

Agami, C ^{[1
]}

Couty, F ^{[1
]}

Rabasso, N ^{[1
]}

机构：

[1] Univ Paris 06, Lab Synthese Asymetr, CNRS, UMR 7611, F-75005 Paris, France

来源：

TETRAHEDRON | 2001年 / 57卷 / 25期

关键词：

heterocycles; alkaloids; stereoselective;

D O I：

10.1016/S0040-4020(01)00458-6

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthetic methodology, based on N-Boc-2-acyloxazolidine chemistry combined with ring-closing metathesis, allows the preparation of enantiopure piperidinic heterocycles showing a 2-(1-hydroxyalkyl) side-chain, a pattern commonly found in natural alkaloids. Synthesis of Delta -3,4-2,6-disubsrituted piperidinic rings can thus be achieved with a good 2,6-cis or -trans stereocontrol, unless the substituent located at Ct is not a phenyl group. Diastereoselective functionnalization of the Delta -3,4 alkene moiety and access to seven or eight-membered nitrogen rings are also key features of this methodology. (C) 2001 Elsevier Science Ltd. All rights reserved.

引用

页码：5393 / 5401

页数：9

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