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Highly Efficient Asymmetric Simmons–Smith Cyclopropanation Promoted by Chiral Heteroorganic Aziridinyl Ligands
Author(s) -
Rachwalski Michał,
Kaczmarczyk Sylwia,
Leśniak Stanisław,
Kiełbasiński Piotr
Publication year - 2014
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.201300883
Subject(s) - cyclopropanation , stereocenter , moiety , aziridine , chemistry , allylic rearrangement , stereochemistry , enantioselective synthesis , medicinal chemistry , catalysis , organic chemistry , ring (chemistry)
Enantiomerically pure heteroorganic catalysts, bearing a hydroxy moiety, a stereogenic sulfinyl group, and a chiral aziridine moiety, have proved highly efficient in the asymmetric Simmons–Smith cyclopropanation of allylic alcohols, which generates the desired products in high yields (up to 95 %) and with ee values up to 94 %. The effect of the stereogenic centers at the sulfinyl sulfur atom and in the aziridine moiety on the stereochemical course of the title reaction is discussed.