Reductive Carbocyclization of Homoallylic Alcohols to syn-Cyclobutanes by a Boron-Catalyzed Dual Ring-Closing Pathway

Chinmoy Kumar Hazra, Jinhoon Jeong, Hyunjoong Kim, Mu Hyun Baik*, Sehoon Park, Sukbok Chang

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

17 Scopus citations

Abstract

The organoborane-catalyzed reductive carbocyclization of homoallylic alcohols has been developed by using hydrosilanes as reducing reagents to provide a range of 1,2-disubstituted arylcyclobutanes. The reaction proceeds in a cis-selective manner with high efficiency under mild conditions. Mechanistic studies, including deuterium scrambling and Hammett studies, and DFT calculations, suggest a dual ring-closing pathway.

Original languageEnglish
Pages (from-to)2692-2696
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number10
DOIs
StatePublished - 1 Mar 2018
Externally publishedYes

Keywords

  • carbocyclization
  • cyclobutanes
  • homoallylic alcohols
  • neighboring-group effects
  • ring-closing

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