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Chiral Brønsted Acid Catalyzed Asymmetric Baeyer–Villiger Reaction of 3‐Substituted Cyclobutanones by Using Aqueous H 2 O 2
Author(s) -
Xu Senmiao,
Wang Zheng,
Zhang Xue,
Zhang Xumu,
Ding Kuiling
Publication year - 2008
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.200705932
Subject(s) - catalysis , aqueous solution , brønsted–lowry acid–base theory , stoichiometry , chemistry , enantioselective synthesis , organic chemistry , aqueous medium , medicinal chemistry
A catalytic amount of a chiral Brønsted acid with aqueous H 2 O 2 as the oxidant is sufficient for the enantioselective Baeyer–Villiger oxidation of 3‐substituted cyclobutanones to give the corresponding γ‐lactones in excellent yields and up to 93 % ee. The method employs benign aqueous H 2 O 2 instead of stoichiometric amounts of a dangerous peracid.