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Molecules 2010, 15(12), 9135-9144; https://doi.org/10.3390/molecules15129135

Unexplored Nucleophilic Ring Opening of Aziridines

1
Instituto de Reconocimiento Molecular y Desarrollo Tecnológico (IDM), Centro Mixto Universidad Politécnica de Valencia, Universidad de Valencia, 46100 Burjassot, Spain
2
Department de Organic Chemistry, Universitat de València, Dr. Moliner 50, 46100 Burjassot, Spain
Dedicated to Professor Carmen Nájera on occasion of her 60th birthday.
*
Author to whom correspondence should be addressed.
Received: 24 November 2010 / Revised: 1 December 2010 / Accepted: 6 December 2010 / Published: 10 December 2010
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Abstract

The reactivity of dianions of carboxylic acids towards aziridines has been studied. Although, a similar reactivity to that of enolates from ketones, esters or amides has been observed, the method directly yields g-aminoacids in one step. The method is complementary of previous results of enenediolate reactivity with other electrophiles. A comparative study with the reactivity of this enediolates with epoxides is included.
Keywords: enediolate; regioselectivity; diastereoselectivity; aziridines; g-aminoacids enediolate; regioselectivity; diastereoselectivity; aziridines; g-aminoacids
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MDPI and ACS Style

Costero, A.M.; Gil, S.; Parra, M.; Rodríguez, P. Unexplored Nucleophilic Ring Opening of Aziridines. Molecules 2010, 15, 9135-9144.

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