Stereoselective alkylation of chiral pyrrolidin-2-ones leading to novel conformationally restricted analogues of 3-methylaspartic acid: A computational investigation

Roberta Galeazzi, Gianluca Martelli, Mario Orena, Samuele Rinaldi

Research output: Contribution to journalArticle

Abstract

The stereoselectivity of the alkylation of chiral pyrrolidin-2-ones leading to conformationally restricted analogues of 3-methylaspartic acid was investigated using density functional theory calculations. The overall stereocontrol is regulated by the relative stability of the lithium enolate intermediates which are also involved in the ratedetermining step leading to the methylaspartic acid derivative. The computed results explain the observed data and the different diastereoselectivity can be ascribed to the nature of the alkylating group.

Original languageEnglish
Pages (from-to)1397-1403
Number of pages7
JournalMonatshefte fur Chemie
Volume143
Issue number10
DOIs
Publication statusPublished - 2012

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Keywords

  • Alkylations
  • Computational chemistry
  • Density functional theory
  • Enolates
  • Reaction mechanism

ASJC Scopus subject areas

  • Chemistry(all)

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