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Synergistic Interplay of a Non‐Heme Iron Catalyst and Amino Acid Coligands in H 2 O 2 Activation for Asymmetric Epoxidation of α‐Alkyl‐Substituted Styrenes
Author(s) -
Cussó Olaf,
Ribas Xavi,
LloretFillol Julio,
Costas Miquel
Publication year - 2015
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.201410557
Subject(s) - catalysis , enantioselective synthesis , chemistry , amino acid , aqueous solution , heme , alkyl , stereochemistry , aqueous medium , medicinal chemistry , combinatorial chemistry , organic chemistry , enzyme , biochemistry
Highly enantioselective epoxidation of α‐substituted styrenes with aqueous H 2 O 2 is described by using a chiral iron complex as the catalyst and N‐protected amino acids (AAs) as coligands. The amino acids synergistically cooperate with the iron center in promoting an efficient activation of H 2 O 2 to catalyze epoxidation of this challenging class of substrates with good yields and stereoselectivities (up to 97 % ee ) in short reaction times.