Chiral Brønsted Acid Catalyzed Asymmetric Baeyer–Villiger Reaction of 3‐Substituted Cyclobutanones by Using Aqueous H 2 O 2 | Zendy

Xu Senmiao | Zendy; Wang Zheng | Zendy; Zhang Xue | Zendy; Zhang Xumu | Zendy; Ding Kuiling | Zendy

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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.

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