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[reaction--see text] A seven-step parallel solution-phase synthesis has been developed for access to ketone-containing mechanism-based cysteine protease inhibitors. The use of liquid-liquid extractions, volatile or solid-supported reagents, and resin-bound scavengers eliminates the need for intermediate column chromatographic purification during this(More)
A rational approach for generating 1,1'-binaphthalene-like axial chirality of a small organic receptor, 2,2'-dihydroxybenzil is presented. The receptor combines with 2 equiv of monodentate primary amines to form a diimine, of which axial chirality is controlled by steric strain with moderate (1.4:1) to good (4.7:1) stereoselectivity. The observed circular(More)
A new type of bicyclic bridgehead phosphoramidites (briphos) is reported, where the geometrical constraints significantly enhance the π-acceptor ability compared with its monocyclic analogs. The briphos is shown to be highly efficient and tunable for Rh(I)-catalyzed conjugate additions of aryl boronic acids to α,β-unsaturated ketones and N-tosyl ketimines.
  • Ansoo Lee, Hyunwoo Kim
  • Journal of the American Chemical Society
  • 2015
A chiral bicyclic bridgehead phosphoramidite (briphos) prepared from 1-aminoindane is a highly efficient and selective ligand for rhodium(I)-catalyzed asymmetric 1,4-addition of arylboronic acids to α,β-unsaturated N,N-dimethyl-sulfamoyl imino esters at ambient temperature. This transformation provides a new class of chiral (Z)-γ,γ-diaryl-α,β-dehydroamino(More)
A mild and efficient dehydrative cross-coupling reaction between allylic alcohols and N-heterocycles using palladium catalysis is reported. A bicyclic bridgehead phosphoramidite (briphos) ligand together with Pd(dba)2 is a highly efficient catalyst, and an acid additive involved in the rate-determining step promotes the catalytic cycle. The coupling(More)
  • Ansoo Lee, Hyunwoo Kim
  • The Journal of organic chemistry
  • 2016
A complementary solution for Rh-catalyzed enantioselective 1,2- and 1,4-arylation with two structurally related chiral ligands is reported. A chiral bicyclic bridgehead phosphoramidite (briphos) ligand derived from 1-aminoindane was efficient for the 1,2-arylation of N-sulfonyl imines, while that derived from 1,2,3,4-tetrahydro-1-naphthylamine was efficient(More)
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