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Enantioselective Insertion of a Carbenoid Carbon into a C–C Bond To Expand Cyclobutanols to Cyclopentanols

Author:
Yada, Akira, Fujita, Shoichiro, Murakami, Masahiro
Source:
Journal of the American Chemical Society 2014 v.136 no.20 pp. 7217-7220
ISSN:
1520-5126
Subject:
carbon, catalysts, chemical bonding, enantiomers, rhodium
Abstract:
When a carbenoid species generated from a tosylhydrazone is reacted with a cyclobutanol in the presence of a chiral rhodium catalyst, a C–C single bond of the cyclobutanol is cleaved, and the carbenoid carbon is inserted therein to furnish a ring-expanded cyclopentanol in an enantioselective manner.
Agid:
5391500