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Isomerization-Free Allylic Alkylations of Terminal π-Allyl Palladium Complexes

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Katja Krämer and Uli Kazmaier*

Institut fr Organische Chemie, Universitt des Saarlandes, D-66123 Saarbrcken, Germany u.kazmaier@mx.uni-saarland.de

J. Org. Chem., 2006, 71 (23), pp 8950–8953

DOI: 10.1021/jo061362d

Publication Date (Web): October 20, 2006

To whom correspondence should be addressed. Tel: 49 681 3023409. Fax: 49 681 3022409.

Abstract

Chelated amino acid ester enolates are excellent nucleophiles for allylic alkylations. With these enolates, even terminal π-allyl palladium complexes react without significant isomerization. This allows a transfer of the cis-olefin geometry from the substrate into the product. Chiral substrates also show a reasonably good 1,5-induction.

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Published In Issue November 10, 2006
Received June 30, 2006

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Isomerization-Free Allylic Alkylations of Terminal π-Allyl Palladium Complexes

Abstract

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History

Recommend & Share

Related Content

An Efficient Synthesis of Terminal Allenes from Terminal 1-Alkynes

Direct Cross-Coupling Reaction of Simple Alkenes with Acrylates Catalyzed by Palladium Catalyst

Total Synthesis and Structure Elucidation of (+)-Phorbasin C

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