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Charge‐Transfer Effect on Chiral Phosphoric Acid Catalyzed Asymmetric Baeyer‐Villiger Oxidation of 3‐Substituted Cyclobutanones Using 30% Aqueous H 2 O 2 as the Oxidant
Author(s) -
Xu Senmiao,
Wang Zheng,
Zhang Xumu,
Ding Kuiling
Publication year - 2010
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201090292
Subject(s) - chemistry , phosphoric acid , intermolecular force , catalysis , acceptor , aryl , combinatorial chemistry , photochemistry , organic chemistry , molecule , alkyl , physics , condensed matter physics
The intermolecular charge‐transfer effect has been employed for the first time as a modulating approach to affect the enantioselectivity in asymmetric catalysis by taking the chiral phosphoric acid catalyzed asymmetric Baeyer‐Villiger oxidation of 3‐aryl cyclobutanones as the reaction prototype. It was found that the electron acceptor additives were able to effectively tune the enantioselectivity via donor‐acceptor interaction with the catalyst and up to 9% enhancement of ee value was observed in a favorable case.