Catalytic asymmetric synthesis of ethyl (1R,2S)-dehydrocoronamate

被引：24

作者：

Fox, Martin E.

Lennon, Ian C.

Farina, Vittorio

机构：

[1] Dowpharma, Chorotech Technol Ltd, Cambridge CB4 0GH, England

[2] Boehringer Ingelheim Pharmaceut Inc, Dept Chem Dev, Ridgefield, CT 06877 USA

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 06期

关键词：

palladium; asymmetric catalysis; allylic alkylation; 3,4-epoxy-l-butene; amino acids;

D O I：

10.1016/j.tetlet.2006.12.025

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A synthesis of (1R,2S)-dehydrocoronamic acid ethyl ester was developed employing a regio- and enantioselective palladium-catalysed nucleophilic ring-opening of 3,4-epoxy-1-butene with a glycine anion equivalent as the key enantiodifferentiating step. The desired selectivity was achieved using Trost's naphthyl ligand. The subsequent activation of the free hydroxyl group and ring-closure by intramolecular S(N)2 reaction gave the desired amino acid ethyl ester. (c) 2006 Elsevier Ltd. All rights reserved.

引用

页码：945 / 948

页数：4

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