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Synfacts 2013; 9(1): 0049
DOI: 10.1055/s-0032-1317774
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart · New York

Enantioselective Baeyer-Villiger Oxidation

Contributor(s):
Hisashi Yamamoto
,
Kimberly Griffin
Zhou L, Liu X, Ji J, Zhang Y, Hu X, Lin L, Feng X * Sichuan University, Chengdu, P. R. of China
Enantioselective Baeyer–Villiger Oxidation: Desymmetrization of Meso Cyclic Ketones and Kinetic Resolution of Racemic 2-Arylcyclohexanones.

J. Am. Chem. Soc. 2012;
134: 17023-17026
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Further Information

Publication History

Publication Date:
17 December 2012 (online)

 
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Key words

Baeyer–Villiger oxidation - scandium - desymmetrization

Significance

The asymmetric Baeyer–Villiger oxidation of prochiral and racemic cyclic ketones effectively synthesized optically active ε- and γ-lactones. The desymmetrization of racemic cyclohexanones interestingly showed a reversal of migratory aptitude with high levels of enantioselectivity.


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Comment

The authors continued their use of chiral N,N′-dioxide-metal catalysts for the Baeyer–­Villiger oxidation reaction. During the desymmetrization of meso-cyclohexanones and meso-cyclo­butanones, the electronic and steric nature of the substituents appeared to have no effect on enantioselectivity; the opposite was true for the kinetic resolution of racemic cyclohexanones.


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