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Cross metathesis reactions of homoallylmethyl malonates with sterically hindered allylic esters (Articolo in rivista)

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Cross metathesis reactions of homoallylmethyl malonates with sterically hindered allylic esters (Articolo in rivista) (literal)

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Alternative label

F. Barile, M. Bassetti, A. D'Annibale, R. Gerometta, M. Palazzi (2011)
Cross metathesis reactions of homoallylmethyl malonates with sterically hindered allylic esters
in European journal of organic chemistry (Print); WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim (Germania)
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Dipartimento di Chimica and IMC-CNR, Università degli Studi di Roma, La Sapienza, P.le Aldo Moro 5, 00185 Roma, Italy (literal)

Titolo

Cross metathesis reactions of homoallylmethyl malonates with sterically hindered allylic esters (literal)

Abstract

The methyl malonate esters of 3-buten-1-ol and 2-methyl-3-buten-1-ol can be coupled efficiently with different methallylic esters in presence of the second generation Grubbs catalyst to yield trisubstituted olefins from the cross metathesis reaction. Product selectivity and yields depend on the relative feedstock stoichiometries and not by the methallylic ester functional group. Alkyl substituents at either the allylic or the geminal position affect significantly the product yields and the E/Z stereoselectivity. (literal)

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