Regio- and stereoselectivity control in palladium-catalyzed allylic alkylation of 1-cycloalkenylmethyl acetates

被引：7

作者：

Jacquet, Olivier ^{[1
]}

Legros, Jean-Yves ^{[1
]}

Coliboeuf, Matthieu ^{[1
]}

Fiaud, Jean-Claude ^{[1
]}

机构：

[1] Univ Paris 11, Ctr Orsay, CNRS, UMR 8182,Inst Chim Mol & Mat Orsay, F-91405 Orsay, France

来源：

TETRAHEDRON | 2008年 / 64卷 / 27期

关键词：

D O I：

10.1016/j.tet.2008.04.059

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Enantiomerically pure allylic acetates 1a and 1b were obtained by lipase-catalyzed acylation through kinetic resolution processes of the racemates. Palladium-catalyzed alkylation of la with dimethyl malonate was both regio- and stereoselective, showing that no isomerization of the acetate la or the intermediate pi-allylic palladium complex took place under the conditions used. Alkylation of 1b was stereoselective but not regioselective. The regioselectivity could be partially controlled by the proper choice of a chiral ligand. Conditions were set up to perform both the alkylation of 1b and the decarbomethoxylation of the resulting product to afford 3-(cyclohex-1-enyl) butanoate in a one-pot, one-step process. (c) 2008 Elsevier Ltd. All rights reserved.

引用

页码：6530 / 6536

页数：7

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