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Synthesis 2004(3): 409-414  
DOI: 10.1055/s-2004-815936
PAPER
© Georg Thieme Verlag Stuttgart · New York

A Cross Metathesis Based Protocol for the Effective Synthesis of Function­alised Allyl Bromides and Chlorides

Marco Bandini, Pier Giorgio Cozzi*, Sebastiano Licciulli, Achille Umani-Ronchi*
Dipartimento di Chimica ‘G. Ciamician’, Università di Bologna, Via Selmi 2, 40126 Bologna, Italy
Fax: +39(51)2099456; e-Mail: piergiorgio.cozzi@ciam.unibo.it; e-Mail: umanironchi@ciam.unibo.it;
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Publication History

Received 3 December 2003
Publication Date:
26 January 2004 (online)

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Abstract

Functionalised allyl halides, useful starting materials for the preparation of substituted organometallic reagents can be simply obtained by a straightforward approach. Hoveyda’s ruthenium carbene catalyst 3, used in catalytic amount (2 mol%), is able to promote the cross metathesis of allyl bromide and chloride with a variety of different substituted olefins giving the corresponding functionalised allyl halides in satisfactory yields. trans-Olefins are obtained as major diastereoisomers reaching 90:10 (trans:cis) ratio when allyl chloride is used as the metathesis partner. This reaction represents a simple and accessible way for the preparation of valuable precursors for functionalised organometallic reagents. In particular, the use of functionalised allyl bromides (10b and 13) in the enantioselective Nozaki-Hiyama reaction promoted by [Cr(Salen)Cl] is presented.

Key words

allyl halides - cross metathesis - ruthenium catalyst - functionalised olefins

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