Delineation of the factors governing reactivity and selectivity in epoxide formation from ammonium ylides and aldehydes |
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Authors: | Robiette Raphaël Conza Matteo Aggarwal Varinder K |
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Institution: | School of Chemistry, University of Bristol, Cantock's Close, Bristol, UKBS6 1TS. |
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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. |
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