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Polystyrene-Supported (2S)-(-)-3-exo-Piperazinoisoborneol: An Efficient Catalyst for the Batch and Continuous Flow Production of Enantiopure Alcohols

Laura Osorio-Planes, Carles Rodríguez-Escrich and Miquel A. Pericàs*

*Institute of Chemical Research of Catalonia (ICIQ), Av. Països Catalans, 16, E-43007 Tarragona, Spain, and Departament de Química Orgànica, Universitat de Barcelona, UB, E-08028, Barcelona, Spain, Email: mapericasiciq.es

L. Osorio-Planes, C. Rodríguez-Escrich, M. A. Pericàs, Org. Lett., 2012, 14, 1816-1819.

DOI: 10.1021/ol300415f (free Supporting Information)


Abstract

A polystyrene-supported analog of 3-exo-morpholinoisoborneol (MIB) offers increased chemical stability as a ligand in the asymmetric alkylation of aldehydes with Et2Zn. The supported ligand turned out to be highly active and enantioselective for a broad scope of substrates, allowing repeated recycling. A single-pass, continuous flow process shows only a marginal decrease in conversion after 30 h of operation.

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Key Words

1,2-additions


ID: J54-Y2012-1010