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Efficient one-pot ring-opening/aldol reactions using (cyclopropyl)methylstannanes

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Leroy, Bernard [UCL]

(Cyclopropyl)methylstannanes, substituted with an electron-withdrawing group, have been found to be effective homo-allylating reagents of aldehydes and ketones. The reaction proceeds by Lewis-acid catalyzed ring opening, followed by an aldol condensation of the resulting enolate, providing homoallylation products in excellent yields. The diastercoselectivity of the process was found to be highly dependent upon the temperature and the solvent, the reaction giving mainly anti adducts at -78 degrees C and syn compounds at 0 'C. (c) 2005 Elsevier Ltd. All rights reserved.

Document type Article de périodique (Journal article) – Article de recherche
Access type Accès restreint
Publication date 2005
Language Anglais
Journal information "Tetrahedron Letters" - Vol. 46, no. 17, p. 3025-3028 (2005)
Peer reviewed yes
Publisher Pergamon-elsevier Science Ltd (Oxford)
issn 0040-4039
e-issn 1873-3581
Publication status Publié
Keywords cyclopropane ; homoallylation ; aldol reaction ; tin
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Bibliographic reference Leroy, Bernard. Efficient one-pot ring-opening/aldol reactions using (cyclopropyl)methylstannanes. In: Tetrahedron Letters, Vol. 46, no. 17, p. 3025-3028 (2005)
Permanent URL http://hdl.handle.net/2078.1/39432