Delineation of the factors governing reactivity and selectivity in epoxide formation from ammonium ylides and aldehydes
(2006) Organic & Biomolecular Chemistry — Vol. 4, n° 4, p. 621-623 (2006)
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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.
- Affiliations
University of Bristol School of Chemistry
Citations
Robiette, R., Conza, M., & Aggarwal, V. K. (2006). Delineation of the factors governing reactivity and selectivity in epoxide formation from ammonium ylides and aldehydes. Organic & Biomolecular Chemistry, 4(4), 621-623. https://doi.org/10.1039/b516926g (Original work published 2006)