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

Abstract : 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.
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https://hal-univ-rennes1.archives-ouvertes.fr/hal-01116012
Contributor : Laurent Jonchère <>
Submitted on : Thursday, February 12, 2015 - 1:20:24 PM
Last modification on : Thursday, March 5, 2020 - 2:06:02 PM

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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, Wiley-VCH Verlag, 2014, 20 (44), pp.14518-23. ⟨10.1002/chem.201403954⟩. ⟨hal-01116012⟩

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