Tunable and highly regio- and diastereoselective vinylogous Mannich-type reaction of dioxinone-derived silyl dienolate.
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.
Gu
Chun-Ling
CL
Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China.
Liu
Li
L
Wang
Dong
D
Chen
Yong-Jun
YJ
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
D000143:Acids; D004146:Dioxanes; D004952:Esters; D012834:Silver