title: Asymmetric disulfonimide-catalyzed synthesis of δ-amino-β-ketoester derivatives by vinylogous Mukaiyama-Mannich reactions.
abstract: An organocatalytic asymmetric synthesis of δ-amino-β-ketoester derivatives has been developed. A chiral disulfonimide (DSI) serves as a highly efficient precatalyst for a vinylogous Mukaiyama-Mannich reaction of readily available dioxinone-derived silyloxydienes with N-Boc-protected imines, delivering products in excellent yields and enantioselectivities. The synthetic utility of this reaction is illustrated in various transformations, including a new CC bond-forming reaction, which provide useful enantioenriched building blocks. The methodology is applied in a formal synthesis of (-)-lasubin.
authors.affiliation: Max-Planck-Institut für Kohlenforschung, Kaiser-Wilhelm-Platz 1, 45470, Mülheim an der Ruhr (Germany).
authors.forename: Qinggang
authors.initials: Q
authors.lastname: Wang
authors.forename: Manuel
authors.initials: M
authors.lastname: van Gemmeren
authors.forename: Benjamin
authors.initials: B
authors.lastname: List
mesh_terms: D000588:Amines / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D007094:Imides / Q000737:chemistry*; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D013450:Sulfones / Q000737:chemistry
chemical_list: D000588:Amines; D004952:Esters; D007094:Imides; D011807:Quinolizines; D013450:Sulfones; C414385:lasubin I
keywords: disulfonimides; organocatalysis; vinylogous Mukaiyama-Mannich reaction; δ-amino-β-ketoesters