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Department of Chemistry, School of Engineering and Science, Jacobs University Bremen, Campus Ring 1, Germany
E-mail: t.nugent@jacobs-university.de
; Fax: +49 421 200 3229
; Tel: +49 421 200 3232
Org. Biomol. Chem., 2011,9, 52-56
DOI:
10.1039/C0OB00822B
Received
04 Oct 2010,
Accepted
06 Oct 2010
First published online
21 Oct 2010
A three component catalyst system entailing an amino acid (OtBu-L-threonine), a hydrogen bond donor (sulfamide), and an amine base (DMAP) allows α-branched aldehyde addition to nitroalkenes in good to high yield and excellent ee. Importantly, the lowest reported catalyst loading (5.0 mol%) and aldehyde stoichiometry (1.2–2.0 equiv) is demonstrated and in most instances the best current product profile is observed.