Protodeboronation of Tertiary Boronic Esters: Asymmetric Synthesis of Tertiary Alkyl Stereogenic Centers

Stefan Nave, Ravindra P. Sonawane, Tim G. Elford, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

149 Citations (Scopus)

Abstract

While tertiary boranes undergo efficient protodeboronation with carboxylic acids, tertiary boronic esters do not. Instead, we have discovered that CsF with 1.1 equiv of H2O (on tertiary diarylalkyl boronic esters) or TBAF center dot 3H(2)O (on tertiary aryldialkyl boronic esters) effect highly efficient protodeboronation of tertiary boronic esters with essentially complete retention of configuration. Furthermore, substituting D2O for H2O provides ready access to deuterium-labeled enantioenriched tertiary alkanes. The methodology has been applied to a short synthesis of the sesquiterpene, (S)-turmerone.

Original languageEnglish
Pages (from-to)17096-17098
Number of pages3
JournalJournal of the American Chemical Society
Volume132
Issue number48
DOIs
Publication statusPublished - 8 Dec 2010

Keywords

  • ENANTIOSELECTIVE SYNTHESIS
  • CHIRAL SECONDARY
  • B-ALKYLCATECHOLBORANES
  • ORGANOBORONIC ESTERS
  • CONJUGATE ADDITIONS
  • ALLYLIC ALKYLATIONS
  • QUATERNARY CARBONS
  • CONVERSION
  • OLEFINS
  • HYDROGENATION

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