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Issue 4, 2006
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Delineation of the factors governing reactivity and selectivity in epoxide formation from ammonium ylides and aldehydes

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Abstract

Diastereoselectivity in reactions of aryl-stabilised ammonium ylides are highly sensitive to the nature of the amine and the ylide substituent. DFT calculations are consistent with a mechanism in which reversibility in betaine formation [despite the high energy (and therefore instability) of ammonium ylides] is finely balanced due to the high barrier to ring closure.

Graphical abstract: Delineation of the factors governing reactivity and selectivity in epoxide formation from ammonium ylides and aldehydes

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Article information


Submitted
29 Nov 2005
Accepted
10 Jan 2006
First published
20 Jan 2006

Org. Biomol. Chem., 2006,4, 621-623
Article type
Communication

Delineation of the factors governing reactivity and selectivity in epoxide formation from ammonium ylides and aldehydes

R. Robiette, M. Conza and V. K. Aggarwal, Org. Biomol. Chem., 2006, 4, 621
DOI: 10.1039/B516926G

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