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.Pubblicazioni consigliate
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