Development of Chiral, Bifunctional Thiosquaramides: Enantioselective Michael Additions of Barbituric Acids to Nitroalkenes

作者:Rombola Michael; Sumaria Chintan S; Montgomery Thomas D; Rawal Viresh H
来源:Journal of the American Chemical Society, 2017, 139(15): 5297-5300.
DOI:10.1021/jacs.7b01115

摘要

We report a general method for the synthesis of chiral thiosquaramides, a class of bifunctional catalysts not previously described in the literature. Thiosquaramides are found to be more acidic and significantly more soluble in nonpolar solvents than their oxosquaramide counterparts, and they are excellent catalysts for the unreported, enantioselective conjugate addition reaction of the barbituric acid pharmacaphore to nitroalkenes, delivering the chiral barbiturate derivatives in high yields and high enantioselectivities, even with catalyst loadings as low as 0.05 mol%.

  • 出版日期2017-4-19