N-Heterocyclic-Carbene-Catalyzed Asymmetric Oxidative Hetero-Diels–Alder Reactions with Simple Aliphatic Aldehydes


  • We thank the NIGMS (GM072586) for support. T.R. thanks Roche and Amgen for support. We thank Donald Gauthier (Merck) for a generous gift of aminoindanol.


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An efficient enantioselective approach to form trans lactams and cis lactones in up to 98 % yield with greater than 99 % ee, and greater than 20:1 d.r. using simple aliphatic aldehydes has been developed. The process involves a new pathway to generate enolate intermediates from aliphatic aldehydes by oxidation and deprotonation. NHC=N-heterocyclic carbene, Ts=4-toluenesulfonyl.