Strain Release of Donor–Acceptor Cyclopropyl Boronate Complexes

Charlotte H. U. Gregson, Venkataraman Ganesh, Varinder K. Aggarwal*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

6 Citations (Scopus)
39 Downloads (Pure)

Abstract

The reactivity of boronate complexes which resemble donor–acceptor cyclopropanes is described. The enantioenriched cyclopropyl boronate complexes were shown to undergo concerted 1,2-metalate rearrangement/ring opening upon activation with a Lewis acid. This method provides atom-efficient access to optically active γ-carbonyl boronic esters in moderate to excellent yields with complete enantiospecificity. Furthermore, a three-component variant of the reaction was established through in situ alkylation, and the synthetic utility of the products as chiral building blocks was demonstrated.
Original languageEnglish
Pages (from-to)3412-3416
Number of pages5
JournalOrganic Letters
Volume21
Issue number9
Early online date24 Apr 2019
DOIs
Publication statusPublished - 3 May 2019

Fingerprint Dive into the research topics of 'Strain Release of Donor–Acceptor Cyclopropyl Boronate Complexes'. Together they form a unique fingerprint.

  • Projects

    Cite this