Enantioselective insertion of a carbenoid carbon into a C-C bond to expand cyclobutanols to cyclopentanols.

J Am Chem Soc

Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan.

Published: May 2014

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.

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Source
http://dx.doi.org/10.1021/ja502229cDOI Listing

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