Syntheses of highly constrained β-aryl isohexanoic acid derivatives via asymmetric Michael addition

Subo Liao, Yinglin Han, Wei Qiu, Michael Bruck, Victor J. Hruby

Research output: Contribution to journalArticle

42 Scopus citations

Abstract

A series of enantiomerically pure highly sterically hindered β-branched isohexanoic acid derivatives have been synthesized with high diastereoselectivity via asymmetric Michael addition. The X-ray crystal structure of (4S,3'S)-3-[3'-(2,6-dimethylphenyl)isohexanyl]-4-phenyl-2-oxazolidinon e demonstrated that the β-configuration was induced from the Si-face, and that the torsional angle χ2 was restricted by the bulky β-isopropyl group to the range expected from molecular modeling.

Original languageEnglish (US)
Pages (from-to)7917-7920
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number44
DOIs
StatePublished - Oct 28 1996

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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