Asymmetric synthesis of chloroisothreonine derivatives via syn-stereoselective Mannich-type additions across N-sulfinyl-α- chloroimines

Gert Callebaut, Filip Colpaert, Melinda Nonn, Loránd Kiss, Reijo Sillanpää, Karl W. Törnroos, Ferenc Fülöp, Norbert De Kimpe, Sven Mangelinckx

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

Mannich-type reactions of O-Boc glycolic esters across chiral N-sulfinyl-α-chloroaldimines resulted in the efficient and syn-stereoselective synthesis of new γ-chloro-α-hydroxy-β-amino esters (dr > 99 : 1). The α-coordinating ability of the chlorine atom was of great importance for the diastereoselectivity of the Mannich-type reaction and overruled the chelation of the sulfinyl oxygen with the lithium ion of the incoming E-enolate in the transition state model. These novel chloroisothreonine derivatives proved to be excellent building blocks in asymmetric synthesis of novel syn-β,γ-aziridino-α-hydroxy esters and biologically relevant trans-oxazolidinone carboxylic esters.

Original languageEnglish
Pages (from-to)3393-3405
Number of pages13
JournalOrganic and Biomolecular Chemistry
Volume12
Issue number21
DOIs
Publication statusPublished - Jun 7 2014

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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