Chiral Brønsted acid catalyzed asymmetric Baeyer-Villiger reaction of 3-substituted cyclobutanones by using aqueous H2O2

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

doi:10.1002/anie.200705932

Chiral Brønsted acid catalyzed asymmetric Baeyer-Villiger reaction of 3-substituted cyclobutanones by using aqueous H₂O₂

Senmiao Xu^*, Zheng Wang, Xue Zhang, Xumu Zhang, Kuiling Ding

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

201 Scopus citations

Abstract

(Chemical Equation Presented) A catalytic amount of a chiral Brønsted acid with aqueous H₂O₂ 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 H₂O₂ instead of stoichiometric amounts of a dangerous peracid.

Original language	English
Pages (from-to)	2840-2843
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	47
Issue number	15
DOIs	https://doi.org/10.1002/anie.200705932
State	Published - 31 Mar 2008
Externally published	Yes

Keywords

Asymmetric catalysis
Cyclobutanones
Hydrogen peroxide
Lactones
Oxidations

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10.1002/anie.200705932

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@article{f010b7a8027e44e2adc38884d567393d,

title = "Chiral Br{\o}nsted acid catalyzed asymmetric Baeyer-Villiger reaction of 3-substituted cyclobutanones by using aqueous H2O2",

abstract = "(Chemical Equation Presented) A catalytic amount of a chiral Br{\o}nsted acid with aqueous H2O2 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 H2O2 instead of stoichiometric amounts of a dangerous peracid.",

keywords = "Asymmetric catalysis, Cyclobutanones, Hydrogen peroxide, Lactones, Oxidations",

author = "Senmiao Xu and Zheng Wang and Xue Zhang and Xumu Zhang and Kuiling Ding",

year = "2008",

month = mar,

day = "31",

doi = "10.1002/anie.200705932",

language = "英语",

volume = "47",

pages = "2840--2843",

journal = "Angewandte Chemie - International Edition",

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publisher = "John Wiley and Sons Ltd",

number = "15",

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TY - JOUR

T1 - Chiral Brønsted acid catalyzed asymmetric Baeyer-Villiger reaction of 3-substituted cyclobutanones by using aqueous H2O2

AU - Xu, Senmiao

AU - Wang, Zheng

AU - Zhang, Xue

AU - Zhang, Xumu

AU - Ding, Kuiling

PY - 2008/3/31

Y1 - 2008/3/31

N2 - (Chemical Equation Presented) A catalytic amount of a chiral Brønsted acid with aqueous H2O2 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 H2O2 instead of stoichiometric amounts of a dangerous peracid.

AB - (Chemical Equation Presented) A catalytic amount of a chiral Brønsted acid with aqueous H2O2 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 H2O2 instead of stoichiometric amounts of a dangerous peracid.

KW - Asymmetric catalysis

KW - Cyclobutanones

KW - Hydrogen peroxide

KW - Lactones

KW - Oxidations

UR - https://www.scopus.com/pages/publications/42249089542

U2 - 10.1002/anie.200705932

DO - 10.1002/anie.200705932

M3 - 文章

C2 - 18324654

AN - SCOPUS:42249089542

SN - 1433-7851

VL - 47

SP - 2840

EP - 2843

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 15

ER -

Chiral Brønsted acid catalyzed asymmetric Baeyer-Villiger reaction of 3-substituted cyclobutanones by using aqueous H₂O₂

Abstract

Keywords

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