Binaphthyl-based structures are “privileged” fragments in organo- and metal-catalyzed processes due to the axial chirality and the ability of this fragment to bear diverse functional catalytic motifs. We have investigated a multifunctional chiral organocatalyst based on binaphthyls, 1,1’-binaphthyl-2-amino-2’-phosphines (MAPs), synthesized from BINOL in 14 steps. This MAP-type catalytic system contains a combination of Brønsted acid, Brønsted base, and Lewis base motifs and has shown acid-switchable activities in complex multistep sequences such as the Morta–Baylis–Hillman (MBH) or aza-MBH reaction with coupled enhancement in both the rate and enantioselectivity (up to 94% ee in 15 minutes). Here we report a new MAP-based catalysis in which the multifunctional organocatalyst also functions as a ligand. Reactions such as MBH, allylic substitution, and Suzuki cross-coupling are investigated as candidates for multicomponent reactions catalyzed by both metal- and organocatalysis.

Multifunctional, MAP-based catalytic systems for cascade reactions and hybrid catalysis

2019 Spring National Meeting

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