Highly diastereoselective and enantiospecific allylation of ketones and imines using borinic esters: Contiguous quaternary stereogenic centers

Jack L Y Chen, Varinder K. Aggarwal*

*Corresponding author for this work

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

79 Citations (Scopus)

Abstract

3,3-Disubstituted allylic boronic esters are not sufficiently reactive to react with ketones and imines. However they can be converted into the corresponding borinic esters by the sequential addition of nBuLi and TFAA. These reactive intermediates possess the perfect balance between reactivity and configurational stability. Their enhanced reactivity allows the highly selective allylation of both ketones and ketimines and facile access to adjacent quaternary stereocenters with full stereocontrol. The versatility of the methodology is demonstrated in the construction of all possible stereoisomers of a quaternary-quaternary motif and by the allylation of the heterocycles dihydroisoquinoline and indole.

Original languageEnglish
Pages (from-to)10992-10996
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number41
DOIs
Publication statusPublished - 6 Oct 2014

Keywords

  • allylic compounds
  • boron
  • diastereoselectivity
  • NMR spectroscopy
  • synthetic methods

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