The organocatalytic synthesis of densely substituted mono- and bis-γ-lactams involving the Mukaiyama Mannich addition of 2,5-bis(trimethylsilyloxy)furan to imines is described. Use of a ditoluenesulfonyl imide produces γ-lactams from mono addition, whereas a more acidic catalyst (triflic acid) produces fused bis-lactams from double addition. Optimized organocatalytic conditions allow for the selective synthesis of either desired core as well as the one-pot, multicomponent assembly of the tri-substituted mono-lactams from aldehydes, amines and bis-trimethylsilyloxyfuran.

Organocatalytic Mukaiyama Mannich reactions of 2,5-bis(trimethylsilyloxy)furan

2019 Fall National Meeting

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