A Stereodivergent Approach to the Synthesis of gem-Diborylcyclopropanes

Nicole Hanania, Molhm Nassir, Nadim Eghbarieh, Ahmad Masarwa*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

We report a designed stereodivergent strategy for the synthesis of gem-diborylcyclopropanes. The reaction provides a highly modular approach to prepare cyclopropane ring variants bearing gem-(Bpin,Bpin), gem-(Bpin,Bdan), and gem-(Bpin,BF3K), with outstanding levels of stereocontrol. This was achieved by diastereoselective Pd-catalyzed cyclopropanation reactions of gem-diborylalkenes with α-diazoarylacetates and α-diazoaryl-trifluoromethyl. The key to the success of this general protocol was the diastereoselective trifluorination reaction of gem-diborylcyclopropanes, followed by the stereospecific interconversion of the trifluoroborate salts into the Bdan group.

Original languageAmerican English
Article numbere202202748
JournalChemistry - A European Journal
Volume28
Issue number72
DOIs
StatePublished - 27 Dec 2022

Bibliographical note

Publisher Copyright:
© 2022 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.

Keywords

  • cyclopropanation
  • diazoacetates
  • gem-dibroylalkanes
  • organoborones
  • stereodivergent-strategy.

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