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Reductive Carbocyclization of Homoallylic Alcohols to syn ‐Cyclobutanes by a Boron‐Catalyzed Dual Ring‐Closing Pathway
Author(s) -
Hazra Chinmoy Kumar,
Jeong Jinhoon,
Kim Hyunjoong,
Baik MuHyun,
Park Sehoon,
Chang Sukbok
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201713285
Subject(s) - cyclobutanes , chemistry , ring strain , catalysis , ring (chemistry) , scrambling , boron , reagent , reductive elimination , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , cycloaddition , linguistics , philosophy
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.