A new class of amine N-oxides derived from trans-2,5-diphenylpyrrolidine were synthesized in enantiomerically pure form and tested as metal-free catalysts in the reaction of aldehydes with allyl(trichloro)silane to afford homoallylic alcohols. The products were obtained in fair to good yields and up to 85% ee. The behavior of structurally different catalysts and the influence of a coordinating unit present in the organocatalyst on controlling the stereochemical efficiency of the reaction were also investigated. Noteworthy a catalyst capable of promoting the allylation of aliphatic aldehydes with an almost unprecedent and unusually high enantioselectivity, up to 85%, was identified.

A new class of chiral Lewis basic metal-free catalysts for stereoselective allylations of aldehydes / V. Simonini, M. Benaglia, L. Pignataro, S. Guizzetti, G. Celentano. - In: SYNLETT. - ISSN 0936-5214. - 2008:7(2008), pp. 1061-1065.

A new class of chiral Lewis basic metal-free catalysts for stereoselective allylations of aldehydes

M. Benaglia;L. Pignataro;S. Guizzetti;G. Celentano
2008

Abstract

A new class of amine N-oxides derived from trans-2,5-diphenylpyrrolidine were synthesized in enantiomerically pure form and tested as metal-free catalysts in the reaction of aldehydes with allyl(trichloro)silane to afford homoallylic alcohols. The products were obtained in fair to good yields and up to 85% ee. The behavior of structurally different catalysts and the influence of a coordinating unit present in the organocatalyst on controlling the stereochemical efficiency of the reaction were also investigated. Noteworthy a catalyst capable of promoting the allylation of aliphatic aldehydes with an almost unprecedent and unusually high enantioselectivity, up to 85%, was identified.
Allyltrichlorosilane; Enantioselective catalysis; Homoallylic alcohol; N-oxides; Organocatalysis
Settore CHIM/06 - Chimica Organica
http://www.thieme-connect.com/ejournals/pdf/synlett/doi/10.1055/s-2008-1072509.pdf
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2434/59787
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