title: Intermediate as catalyst: catalytic asymmetric conjugate addition of nitroalkanes to α,β-unsaturated thioamides.
abstract: Catalytic asymmetric conjugate addition of nitroalkanes to α,β-unsaturated thioamides is promoted by a mesitylcopper/(R)-DTBM-Segphos precatalyst, affording γ-nitrothioamides in moderate to high syn-selectivity and excellent enantioselectivity. The intermediate Cu-thioamide enolate functions as a soft Lewis acid/hard Brønsted base cooperative catalyst to drive the catalytic cycle efficiently under proton transfer conditions.
authors: Institute of Microbial Chemistry, Tokyo, 3-14-23 Kamiosaki, Tokyo 141-0021, Japan.
authors: Takanori
authors: T
authors: Ogawa
authors: Shinsuke
authors: S
authors: Mouri
authors: Ryo
authors: R
authors: Yazaki
authors: Naoya
authors: N
authors: Kumagai
authors: Masakatsu
authors: M
authors: Shibasaki
mesh_terms: D000473:Alkanes / Q000737:chemistry*; D002384:Catalysis; D008958:Models, Molecular; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D013237:Stereoisomerism; D013854:Thioamides / Q000737:chemistry*
chemical_list: D000473:Alkanes; D013854:Thioamides; D009584:Nitrogen