Amino-zinc-ene-enolate cyclisation:: a short access to (2S,3R)- and (2S,3R)-3-benzylprolines (3-benzylpyrrolidine-2-carboxylic acids)

被引：11

作者：

Quancard, J ^{[1
]}

Magellan, H ^{[1
]}

Lavielle, S ^{[1
]}

Chassaing, G ^{[1
]}

Karoyan, P ^{[1
]}

机构：

[1] Univ Paris 06, UMR CNRS 7613, F-75252 Paris 05, France

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 10期

关键词：

amino-zinc-ene-enolate cyclisation;

D O I：

10.1016/j.tetlet.2004.01.039

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of 3-benzylprolines can be easily achieved in a diastereoselective and enantioselective way via amino-zincene-enolate cyclisation. Transmetalation of the cyclic zinc intermediate with Pd-2(dba)(3)/P(o-Tolyl)(3) allowed functionalisation with an aromatic ring. One-pot hydrogenolysis and Boc-protection led to the cis-isomer readily usable for peptide synthesis. The transisomer was obtained by epimerisation of the alpha-centre in a sealed tue Lit 200 degreesC. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：2185 / 2187

页数：3

共 16 条

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