A highly diastereoselective Tandem radical reaction. Facile three-component routes to protected (E)-polysubstituted homoallylic alcohols

Yeong Jiunn Jang, Jhenyi Wu, Yung Feng Lin, Ching Fa Yao

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

A facile synthesis of geometrically pure (E)-1,2,4-trisubstituted and (E)-1,2,4-tetrasubstituted homoallylic benzoates was developed. Various Lewis acids were subsequently evaluated in the diastereoselective radical substitution of (E)-β-nitrostyrene, and Titanium (IV) 2-ethylhexoxide emerged as the best Lewis acid in terms of yield and diastereoselectivity (up to 98% de). These reactions occurred with high regio-, diastereo- and stereoselectivity, and a possible mechanism to explain this transformation was proposed.

Original languageEnglish
Pages (from-to)6565-6574
Number of pages10
JournalTetrahedron
Volume60
Issue number31
DOIs
Publication statusPublished - 2004 Jul 26

Keywords

  • (E)-β-Nitrostyrene
  • Diastereoselective
  • Homoallylic alcohol
  • Radical

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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