Lithium-Boron Chemistry: A Synergistic Strategy in Modern Synthesis

Charlotte G Watson*, Phillip J Unsworth, Daniele Leonori, Varinder K Aggarwal

*Corresponding author for this work

Research output: Chapter in Book/Report/Conference proceedingChapter in a book

5 Citations (Scopus)

Abstract

Organoboranes and boronic esters react with nucleophiles to give an intermediate boronate complex. If the nucleophile contains a good enough leaving group, a 1,2-metallate rearrangement takes places resulting in the homologation of the starting boron species. A broad range of achiral and chiral organoborons can be homologated using enantioenriched lithiated carbamates with excellent stereospecificity. The homologated chiral boron species can then undergo further homologations, often in a one-pot process, or be converted into alternative functional groups. The factors responsible for stereocontrol are described and applications of the methodology in total synthesis are illustrated.

Original languageEnglish
Title of host publicationLithium Compounds in Organic Synthesis
Subtitle of host publicationFrom Fundamentals to Applications
EditorsR. Luisi, V. Capriati
Place of PublicationWeinheim, Germany
PublisherWiley-Blackwell
Pages397-422
Number of pages26
ISBN (Print)9783527667512, 9783527333431
DOIs
Publication statusPublished - 9 Apr 2014

Structured keywords

  • BCS and TECS CDTs

Keywords

  • Borylation
  • Carbamates
  • Carbenoids
  • Lithiation
  • Organolithiums
  • Stereospecific
  • Total synthesis

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