Functionalized allyl halides, useful starting materials for the prepn. of substituted organometallic reagents can be simply obtained by a straightforward approach. Hoveyda's ruthenium carbene catalyst, used in catalytic amt. (2 mol%), is able to promote the cross metathesis of allyl bromide and chloride with a variety of different substituted olefins giving the corresponding functionalized 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 prepn. of valuable precursors for functionalized organometallic reagents. In particular, the use of functionalized allyl bromides in the enantioselective Nozaki-Hiyama reaction promoted by [Cr(Salen)Cl] is presented.

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

BANDINI, MARCO;COZZI, PIER GIORGIO;MELCHIORRE, PAOLO;LICCIULLI, SEBASTIANO;UMANI RONCHI, ACHILLE
2004

Abstract

Functionalized allyl halides, useful starting materials for the prepn. of substituted organometallic reagents can be simply obtained by a straightforward approach. Hoveyda's ruthenium carbene catalyst, used in catalytic amt. (2 mol%), is able to promote the cross metathesis of allyl bromide and chloride with a variety of different substituted olefins giving the corresponding functionalized 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 prepn. of valuable precursors for functionalized organometallic reagents. In particular, the use of functionalized allyl bromides in the enantioselective Nozaki-Hiyama reaction promoted by [Cr(Salen)Cl] is presented.
M. Bandini; P.G. Cozzi; P. Melchiorre; S. Licciulli; A. Umani-Ronchi
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11585/7981
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