Stereoselective allylboration using (B)-γ- alkoxyallyldiisopinocampheylboranes: Highly selective reactions for organic synthesis

J. Subash Chandra, M. Venkat Ram Reddy

Research output: Contribution to journalReview article

3 Scopus citations

Abstract

This review describes the synthesis of novel alkoxyallylborane reagents derived from α-pinene and their applications in stereoselective total synthesis of natural products. These reagents can be conveniently prepared and react readily with a wide variety of aldehydes and imines to provide the corresponding α-alkoxy substituted homoallylic alcohols/amines respectively. The (Z)-γ-alkoxyallylborane reagents provide 1,2-syn α-alkoxy homoallylic alcohols/amines while the corresponding (E)-γ-alkoxyallylborane reagents furnish 1,2-anti products exclusively in very high enantioselectivities.

Original languageEnglish (US)
Pages (from-to)121-144
Number of pages24
JournalArkivoc
Volume2007
Issue number2
DOIs
StatePublished - May 15 2007

Keywords

  • 1,2-syn diols
  • Alkoxyallylboration
  • Allylboration
  • Diisopinocampheylborane
  • Homoallylic alcohol
  • Protecting groups
  • α-alkoxy-homoallylic alcohols
  • α-pinene

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