An asymmetric organocatalytic approach to Michael reactions of thiazolones and nitroalkenes: Preparation of compounds with anti-cancer potency

Article abstract of DOI:10.1002/ejoc.201201094

We present a highly efficient strategy for obtaining a series of chiral 2,4-disubstituted thiazolone derivatives with excellent diastereo-and enantioselectivities through the creation of carbon-and nitrogen-substituted quaternary carbon stereocenters. With the chiral tertiary amine-thiourea catalyst developed by our group, the reactions could be performed smoothly at 1 mol-% catalyst loadings without any additive. Preliminary biological evaluation demonstrated that these analogues could inhibit cell proliferation in vitro significantly.