Synthetic utility of N-sulfonylimines

Abstract

(A) Catalytic hydrogenation of methyl vinyl ketone and ethyl vinyl ketone in the presence of N-(2-nitrophenylsulfonyl)imines at ambient pressure with tri-2-furylphosphine ligand rhodium catalysts produces the mannich product with moderate to good syndiasteroselectivity.12 (Chemical Equation Presented) (B) Direct asymmetric mannich-type reaction of N-sulfonylimines with trichloromethylketone in the presence of lanthanum aryloxide and Pybox gives β-amino carbonyl compounds.13 (Chemical Equation Presented) (C) Selective reduction of electronically deficient imines in the presence of ketones, Et3Zn, and Ni(acac)2 produces respective amines in moderate to good yields.14 (Chemical Equation Presented) (D) The catalytic mannich reaction of 1,1-difluoro-2-trialkyl(aryl)-silyl-2- trimethylsilyloxyethenes with sulfonylimines gives α,α-difluoro- β-amino acid derivatives.15 (Chemical Equation Presented) (E) The reaction of phosphorylated N-sulfonylimines with hydrophosphoryl agents involve the C-N transfer of phosphoryl group and produce aza-Perkow products.16 (Chemical Equation Presented) (F) In the presence of a catalytic amount of chiral diaminothiophosphoramide the asymmetric addition of diethyl zinc to Nsulfonylimines can be achieved in moderate to good yield ee (63-93%).17 (Chemical Equation Presented) (G) The nucleophillic addition of chiral lithium enolates of (S)-(-)-4-benzyl-2-oxazolidinone acetamide with N-tosylarylaldehyde imines gives β-aryl-β-amino acid derivatives in good to excellent diastereoselectivity.18 (Chemical Equation Presented). © Georg Thieme Verlag Stuttgart.