Cross-metathesis/isomerization/allylboration sequence for a diastereoselective synthesis of anti-homoallylic alcohols from allylbenzene derivatives and aldehydes. - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2014

Cross-metathesis/isomerization/allylboration sequence for a diastereoselective synthesis of anti-homoallylic alcohols from allylbenzene derivatives and aldehydes.

Résumé

We describe a highly diastereoselective approach to anti-homoallylic alcohols from allylbenzene derivatives and aldehydes. The strategy is based on a cross-metathesis/isomerization/allylboration sequence catalyzed successively by ruthenium and iridium. This methodology provides another way to access this class of compounds, which leads to the preparation of hitherto-unknown homoallylic alcohols without the requirement to control the stereochemistry of the 1-alkenyl boronate intermediates. Our study towards an enantioselective version of this sequential reaction is also reported.

Domaines

Chimie

Dates et versions

hal-01116012 , version 1 (12-02-2015)

Identifiants

Citer

Rémy Hemelaere, François Carreaux, Bertrand Carboni. Cross-metathesis/isomerization/allylboration sequence for a diastereoselective synthesis of anti-homoallylic alcohols from allylbenzene derivatives and aldehydes.. Chemistry - A European Journal, 2014, 20 (44), pp.14518-23. ⟨10.1002/chem.201403954⟩. ⟨hal-01116012⟩
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