Volume 126, Issue 36 pp. 9776-9780
Zuschrift

Asymmetric Synthesis of Highly Substituted β-Lactones through Oxidative Carbene Catalysis with LiCl as Cooperative Lewis Acid

Srikrishna Bera

Srikrishna Bera

Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster (Germany)

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Dr. Ramesh C. Samanta

Dr. Ramesh C. Samanta

Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster (Germany)

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Dr. Constantin G. Daniliuc

Dr. Constantin G. Daniliuc

Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster (Germany)

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Prof. Dr. Armido Studer

Corresponding Author

Prof. Dr. Armido Studer

Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster (Germany)

Organisch-Chemisches Institut, Westfälische Wilhelms-Universität Münster, Corrensstraße 40, 48149 Münster (Germany)Search for more papers by this author
First published: 11 July 2014
Citations: 49

This work was financially supported by the NRW Graduate School of Chemistry and the SFB 858.

Abstract

The reaction of enals with β-diketones, β-ketoesters, and malonates bearing a β-oxyalkyl substituent at the α-position by oxidative NHC catalysis to provide highly substituted β-lactones is described. Reactions occur with excellent diastereo- and enantioselectivity. The organo cascade comprises two CC bond formations and one CO bond formation. Up to four contiguous stereogenic centers including two fully substituted stereocenters are formed in the cascade.

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