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Stereoselective synthesis of functionalised triol units by SnCl4 promoted allylation of alpha-benzyloxyaldehydes: crucial role of the stoichiometry of the Lewis acid

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Dubost, C Declercq, Jean-Paul [UCL] Leroy, Bernard [UCL] Marko, Istvan [UCL] Tinant, Bernard [UCL] Bryans, J

Enantiomerically pure syn-anti and syn-syn configured triol units are efficiently synthesized by the SnCl4 mediated allylation of chiral alpha-benzyloxyaldehydes with the uniquely functionalised allylstannane 9. Remarkably, the stereochemistry of the adducts is solely governed by the amount of Lewis acid employed. (C) 2004 Elsevier Ltd. All rights reserved.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2004
Language Anglais
Journal information "Tetrahedron" - Vol. 60, no. 35, p. 7693-7704 (2004)
Peer reviewed yes
Publisher Pergamon-elsevier Science Ltd (Oxford)
issn 0040-4020
e-issn 1464-5416
Publication status Publié
Affiliation UCL - SC/CHIM - Département de chimie
Keywords allylation ; allylstannane ; chelation ; triols ; stereocontrol ; Lewis acid
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Bibliographic reference Dubost, C ; Declercq, Jean-Paul ; Leroy, Bernard ; Marko, Istvan ; Tinant, Bernard ; et. al. Stereoselective synthesis of functionalised triol units by SnCl4 promoted allylation of alpha-benzyloxyaldehydes: crucial role of the stoichiometry of the Lewis acid. In: Tetrahedron, Vol. 60, no. 35, p. 7693-7704 (2004)
Permanent URL http://hdl.handle.net/2078.1/40020