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Synfacts 2009(8): 0922-0922  
DOI: 10.1055/s-0029-1217587
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

SOMO Activation/α-Chlorination: From Aldehydes to Terminal Epoxides

Contributor(s): Benjamin List, Corinna Reisinger
M. Amatore, T. D. Beeson, S. P. Brown, D. W. C. MacMillan*
Merck Center for Catalysis at Princeton University, USA
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Publikationsdatum:
23. Juli 2009 (online)

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Significance

The authors report a new approach to the enantioselective α-chlorination of aldehydes 1 using SOMO catalysis. In the presence of imidazolidinone salt 2 (20 mol%), an oxidant combination consisting of Cu(TFA)2 (50 mol%) and stoi­chiometric Na2S2O8, and LiCl as the chlorine source, various α-chloro aldehydes 3 were obtained in high yields and enantioselectivities. This transformation was further exploited as part of a linchpin catalysis approach to enantioenriched terminal epoxides 4 in a one-pot, three-step sequence comprising α-chlorination, reduction, and ring closure to give the epoxide.