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Synfacts 2009(2): 0209-0209  
DOI: 10.1055/s-0028-1087597
Organo- and Biocatalysis
© Georg Thieme Verlag Stuttgart ˙ New York

α-Alkylation of Aldehydes with Styrenes

Contributor(s): Benjamin List, Ilija Èorić
T. H. Graham, C. M. Jones, N. T. Jui, D. W. C. MacMillan*
Merck Center for Catalysis at Princeton University, New Jersey, USA
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Publication History

Publication Date:
22 January 2009 (online)

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Significance

For the first time styrenes are used as α-alkylation partners for aldehydes. With a catalytic amounts of secondary amine 1 salt and ceric ammonium nitrate (CAN) as a stoichiometric oxidant, γ-nitrate-α-alkyl aldehydes 2 are obtained in high yield with excellent enantioselectivity. The synthetic value of these products is demonstrated by the simple conversion into homobenzylated aldehyde 3, and heterocycles 4-7 without erosion of enantiomeric ratios.