Stereocontrolled synthesis of a prototype library of enantiopure 2,4-disubstituted 4-aryl-6-piperidinones and piperidines

被引：19

作者：

Hanessian, S

van Otterlo, WAL

Nilsson, I

Bauer, U

机构：

[1] Univ Montreal, Dept Chem, Montreal, PQ H3C 3J7, Canada

[2] AstraZeneca, Molndal, Sweden

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 11期

基金：

加拿大自然科学与工程研究理事会;

关键词：

piperidine; conjugate cuprate addition;

D O I：

10.1016/S0040-4039(02)00184-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Addition of a set of aryl cuprates to N-Boc O-TBDPS 2-hydroxymethyl 3.4-unsaturated 6-piperidinones affords syn-adducts in preference to anti when mixed Grignard-cuprates are used. Aryllithio cuprates give more of the anti-isomer in some cases. A library of 2-hydroxymethyl carbamates (27 compounds) and 2-hydroxymethyl aryl ethers and thioethers (19 compounds) was generated from a selection of 4-aryl-6-piperidinones, and some were further reduced to the corresponding piperidines (9 compounds). (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：1995 / 1998

页数：4

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