Straightforward entry to the pipecolic acid nucleus.: Enantioselective synthesis of baikiain

被引：50

作者：

Ginesta, X ^{[1
]}

Pericàs, MA ^{[1
]}

Riera, A ^{[1
]}

机构：

[1] Dept Quim Organ, E-08028 Barcelona, Spain

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 05期

关键词：

D O I：

10.1016/S0040-4039(01)02271-7

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

New enantioselective syntheses of N-protected baikiain and pipecolic acid have been developed. The starting material is 2,3-epoxy-5-hexen-1-ol (4) readily available in high ee by Sharpless epoxidation. The regio- and stereoselective epoxide ring-opening by allylamine afforded a doubly unsaturated amine that was converted into a carbamate (Boc) and submitted to ring-closing metathesis. The resulting cyclic amino diol 6 is a key intermediate that was converted into N-Boc-baikiain and several pipecolic acid derivatives. (C) 2002 Elsevier Science Ltd. All rights reserved.

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页码：779 / 782

页数：4

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