Subscribe to RSS
α-Alkylation of Aldehydes with Styrenes
T. H. Graham, C. M. Jones, N. T. Jui, D. W. C. MacMillan*
Merck Center for Catalysis at Princeton University, New Jersey, USA
22 January 2009 (online)
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.