title: Tunable and highly regio- and diastereoselective vinylogous Mannich-type reaction of dioxinone-derived silyl dienolate.
abstract: A tunable and highly regio- and diastereoselective vinylogous Mannich-type reaction of dioxinone-derived silyl dienolate (1) with chiral N-tert-butanesulfinyl imino ester (2) was developed. By appropriate choice of Lewis acid catalyst, two diastereomers of the gamma-product were obtained, respectively, with dr up to 95:5. The procedure for the Ag(I)-catalyzed vinylogous Mannich-type reaction also provided facile access to the alpha-regioisomer with excellent diastereoselectivities (up to >99:1 dr) by changing the counterion of the Ag(I) salt.
authors.affiliation: Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
authors.forename: Chun-Ling
authors.initials: CL
authors.lastname: Gu
authors.forename: Li
authors.initials: L
authors.lastname: Liu
authors.forename: Dong
authors.initials: D
authors.lastname: Wang
authors.forename: Yong-Jun
authors.initials: YJ
authors.lastname: Chen
mesh_terms: D000143:Acids / Q000737:chemistry; D002384:Catalysis; D004146:Dioxanes / Q000737:chemistry*; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D012834:Silver / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000143:Acids; D004146:Dioxanes; D004952:Esters; D012834:Silver