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Synfacts 2009(2): 0169-0169  
DOI: 10.1055/s-0028-1087629
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Carbonyl-Ene Reaction Catalyzed by N,N′-Dioxide-Nickel(II) Complex

Contributor(s): Hisashi Yamamoto, Joshua N. Payette
K. Zheng, J. Shi, X. Liu, X. Feng*
Sichuan University, Chengdu, P. R. of China
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Publication History

Publication Date:
22 January 2009 (online)

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Significance

As early as 1988, Yamamoto and colleagues demonstrated the first example of an asymmetric carbonyl-ene reaction of aldehydes using an organoalumnium complex (Tetrahedron Lett. 1988, 29, 3967). Subsequently, a large body of work on this reaction has appeared with particular focus on glyoxolates as substrates. In the present study the authors apply a chiral N,N′-dioxide-nickel(II) complex to a wide range of glyoxal derivatives as well as glyoxolates with various aryl and aliphatic alkenes. A very large number of examples is provided to demonstrate the scope and generality of the system. Products are obtained in consistently high yields and excellent enantioselectivities.