Premium
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 international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201713285
Subject(s) - cyclobutanes , chemistry , catalysis , ring strain , ring (chemistry) , boron , scrambling , reagent , combinatorial chemistry , stereochemistry , medicinal chemistry , organic chemistry , linguistics , philosophy , cycloaddition
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.