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 language | English |
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Pages (from-to) | 2692-2696 |
Number of pages | 5 |
Journal | Angewandte Chemie - International Edition |
Volume | 57 |
Issue number | 10 |
DOIs | |
State | Published - 1 Mar 2018 |
Externally published | Yes |
Keywords
- carbocyclization
- cyclobutanes
- homoallylic alcohols
- neighboring-group effects
- ring-closing