Synfacts 2011(5): 0560-0560  
DOI: 10.1055/s-0030-1259861
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

Enantioselective β-Functionalization of Aldehydes via Oxidative Enamine Catalysis

Contributor(s): Benjamin List, Ji-Woong Lee
S.-L. Zhang, H.-X. Xie, J. Zhu, H. Li, X.-S. Zhang, J. Li*, W. Wang*
University of New Mexico, Albuquerque, USA; Shanghai Institute of Materia Medica and East China University of Science and Technology, Shanghai, P. R. of China
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
15. April 2011 (online)

Significance

The authors expand enamine-­iminium catalysis for the β-functionalization of aldehydes via enamine oxidation. By using a stoichiometric amount of an oxidant (e.g., IBX), in situ generated enamines are oxidized to the corresponding α,β-unsaturated iminium ions, which ­undergo Michael reactions with moderate yields and good to excellent enantioselectivities. The synthetic potential of this methodology is also demonstrated by conducting various cascade ­reactions, which give rise to complex chiral building blocks from simple aldehydes. In the absence of a nucleophile, the authors could observe the corresponding α,β-unsaturated enal, which is formed via hydrolysis of the iminium intermediate.