Stereospecific 1,2‐Migrations of Boronate Complexes Induced by Electrophiles

Hui Wang, Changcheng Jing, Adam Noble, Varinder Kumar Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)peer-review

16 Downloads (Pure)

Abstract

The stereospecific 1,2‐migration of boronate complexes is one of the most representative reactions in boron chemistry. This process has been used extensively to develop powerful methods for asymmetric synthesis, with applications spanning from pharmaceuticals to natural products. Typically, 1,2‐migration of boronate complexes is driven by displacement of an α ‐leaving group, oxidation of an α ‐boryl radical, or electrophilic activation of an alkenyl boronate complex. The aim of this article is to summarize the recent advances in the rapidly expanding field of electrophile‐induced stereospecific 1,2‐migration of groups from boron to sp 2 and sp 3 carbon centers. It will be shown that three different conceptual approaches can be utilized to enable the 1,2‐migration of boronate complexes: stereospecific Zweifel‐type reactions, catalytic conjunctive coupling reactions, and transition metal‐free sp 2 ‐ sp 3 couplings. A discussion of the reaction scope, mechanistic insights, and synthetic applications of the work described is also presented.
Original languageEnglish
Number of pages15
JournalAngewandte Chemie - International Edition
Early online date22 Jul 2020
DOIs
Publication statusE-pub ahead of print - 22 Jul 2020

Keywords

  • Boron
  • stereospecific
  • Zweifel olefination
  • Chiral
  • asymmetric synthesis

Fingerprint

Dive into the research topics of 'Stereospecific 1,2‐Migrations of Boronate Complexes Induced by Electrophiles'. Together they form a unique fingerprint.

Cite this