title: Direct Catalytic Asymmetric Conjugate Addition of Saturated and Unsaturated Thioamides.
abstract: Direct catalytic asymmetric conjugate addition of thiolactams to α,β-unsaturated thioamides was efficiently promoted by a soft Lewis acid/hard Brønsted base cooperative catalyst in a highly stereocontrolled manner. Thioamide functionality was crucial to promote both the efficient enolization of thiolactam pronucleophiles and the subsequent stereoselective conjugate addition to α,β-unsaturated thioamides. Differential manipulation of the two thioamide functionalities of the product highlights the synthetic utility of the present catalytic system.
authors.affiliation: †Institute of Microbial Chemistry (BIKAKEN), Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan.
authors.forename: Nilanjana
authors.initials: N
authors.lastname: Majumdar
authors.affiliation: †Institute of Microbial Chemistry (BIKAKEN), Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan.
authors.forename: Akira
authors.initials: A
authors.lastname: Saito
authors.affiliation: †Institute of Microbial Chemistry (BIKAKEN), Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan.
authors.forename: Liang
authors.initials: L
authors.lastname: Yin
authors.affiliation: †Institute of Microbial Chemistry (BIKAKEN), Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan.
authors.forename: Naoya
authors.initials: N
authors.lastname: Kumagai
authors.affiliation: †Institute of Microbial Chemistry (BIKAKEN), Tokyo, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan.|‡JST, ACT-C, 3-14-23 Kamiosaki, Shinagawa-ku, Tokyo 141-0021, Japan.
authors.forename: Masakatsu
authors.initials: M
authors.lastname: Shibasaki
mesh_terms: D002384:Catalysis; D007769:Lactams / Q000737:chemistry*; D058116:Lewis Acids / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism; D013854:Thioamides / Q000737:chemistry*
chemical_list: D007769:Lactams; D058116:Lewis Acids; D013854:Thioamides