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Substrate‐Controlled Cyclopropanation Reactions of Glycals with Aryl Diazoacetates
Author(s) -
Guo Yujing,
Pei Chao,
Koenigs Rene M.
Publication year - 2020
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.202000569
Subject(s) - cyclopropanation , stereoselectivity , glucal , substrate (aquarium) , chemistry , catalysis , aryl , glycosylation , acceptor , glycal , combinatorial chemistry , organic chemistry , biology , biochemistry , physics , ecology , alkyl , condensed matter physics
Cyclopropanation reactions of d ‐glucal and d ‐galactal derivatives with aryldiazoacetates can be conducted in a substrate‐controlled, stereoselective fashion using simple Rh(II) catalysts, which is further supported by DFT studies. Following this methodology, sugar‐derived, donor‐acceptor cyclopropanes can be accessed that allow stereoselective O ‐glycosylation reactions.