Asymmetric Synthesis of Secondary and Tertiary Boronic Esters

Beatrice S.L. Collins, Claire M. Wilson, Eddie L. Myers, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalReview article (Academic Journal)

96 Citations (Scopus)
366 Downloads (Pure)

Abstract

Non-racemic chiral boronic esters are recognised as immensely valuable building blocks in modern organic synthesis. Their stereospecific transformation into a variety of functional groups—from amines and halides to arenes and alkynes—along with their air and moisture stability, has established them as an important target for asymmetric synthesis. Efforts towards the stereoselective synthesis of secondary and tertiary alkyl boronic esters have spanned over five decades and are underpinned by a wealth of reactivity platforms, drawing on the unique and varied reactivity of boron. This Review summarizes strategies for the asymmetric synthesis of alkyl boronic esters, from the seminal hydroboration methods of H. C. Brown to the current state of the art.

Original languageEnglish
Pages (from-to)11700-11733
Number of pages34
JournalAngewandte Chemie - International Edition
Volume56
Issue number39
Early online date9 Aug 2017
DOIs
Publication statusPublished - 18 Sep 2017

Keywords

  • asymmetric synthesis
  • boronic esters
  • synthetic methods

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