title: Direct catalytic asymmetric vinylogous conjugate addition of unsaturated butyrolactones to α,β-unsaturated thioamides.
abstract: Soft Lewis acid/Brønsted base cooperative catalysts have enabled direct catalytic asymmetric vinylogous conjugate addition of α,β- and β,γ-unsaturated butyrolactones to α,β-unsaturated thioamides with perfect atom economy. When using α-angelica lactone and its derivatives as pronucleophiles, as little as 0.5 mol% catalyst loading was sufficient to complete the reaction necessary to construct consecutive tri- and tetrasubstituted stereogenic centers in a highly diastereo- and enantioselective fashion.
authors.affiliation: Institute of Microbial Chemistry (BIKAKEN), 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021 (Japan) http://www.bikaken.or.jp/research/group/shibasaki/shibasaki-lab/index_e.html.
authors.forename: Liang
authors.initials: L
authors.lastname: Yin
authors.forename: Hisashi
authors.initials: H
authors.lastname: Takada
authors.forename: Shaoquan
authors.initials: S
authors.lastname: Lin
authors.forename: Naoya
authors.initials: N
authors.lastname: Kumagai
authors.forename: Masakatsu
authors.initials: M
authors.lastname: Shibasaki
mesh_terms: D015107:4-Butyrolactone / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D058116:Lewis Acids / Q000737:chemistry; D013237:Stereoisomerism; D013854:Thioamides / Q000737:chemistry*
chemical_list: D058116:Lewis Acids; D013854:Thioamides; D003300:Copper; D015107:4-Butyrolactone
keywords: Michael addition; asymmetric catalysis; copper; heterocycles; synthetic methods