Stereoselective synthesis of vic-halohydrins via l-tert-leucine-catalyzed syn-selective aldol reaction

Atsushi Umehara, Takuya Kanemitsu, Kazuhiro Nagata, Takashi Itoh

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

L-tert-Leucine was found to be an effective organocatalyst for the asymmetric aldol reaction of chloroacetone. The stereoselective synthesis of vic-halohydrins was accomplished with excellent regioselectivity (>99%) to generate α-chloro-β-hydroxy ketones with high syn selectivity (syn/anti = 16:1) and enantioselectivity (up to 95% ee).

Original languageEnglish
Pages (from-to)453-457
Number of pages5
JournalSynlett
Issue number3
DOIs
Publication statusPublished - 2012 Jan 19
Externally publishedYes

Keywords

  • aldol reaction
  • amino acids
  • asymmetric synthesis
  • chloroacetone
  • organocatalysis

ASJC Scopus subject areas

  • Organic Chemistry

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