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Synfacts 2009(10): 1155-1155  
DOI: 10.1055/s-0029-1217948
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Desymmetrization of meso-Cyclopentanones

Contributor(s): Benjamin List, Corinna Reisinger
G. Dickmeiss, V. De Sio, J. Udmark, T. B. Poulsen, V. Marcos, K. A. Jørgensen*
Aarhus University, Denmark
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Publication History

Publication Date:
22 September 2009 (online)

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Significance

Jørgensen and co-workers have achieved the asymmetric desymmetrizing fragmentation of meso-cyclopropane cyclopentanone (1) and epoxide-allylic alcohol rearrangements of meso-epoxy cyclopentanone (3) in the presence of thiourea-modified cinchona alkaloid derivatives (catalyst A or B) via an E1cb-like mechanism. The concept was exploited in asymmetric one-pot and tandem desymmetrizing epoxide-allylic alcohol rearrangement-Michael addition sequences of epoxycyclopentanone (3, R = H) by performing the reaction in the presence of thiol and malonate nucleophiles or prior to a rhodium-catalyzed vinylation. A kinetic resolution of 5 by means of this method is also presented.