title: Stereocontrolled synthesis of bicyclic sulfamides via Pd-catalyzed alkene carboamination reactions. Control of 1,3-asymmetric induction by manipulating mechanistic pathways.
abstract: A new annulation strategy for the synthesis of trans-bicyclic sulfamides is described. The Pd-catalyzed alkene carboamination reactions of 2-allyl and cis-2,5-diallyl pyrrolidinyl sulfamides with aryl and alkenyl triflates afford the fused bicyclic compounds in good yields and with good diastereoselectivity (up to 13:1 dr). Importantly, by employing reaction conditions that favor an anti-aminopalladation mechanism, the relative stereochemistry between the C3 and C4a stereocenters of the products is reversed relative to related Pd-catalyzed carboamination reactions that proceed via syn-aminopalladation.
authors.affiliation: Department of Chemistry, University of Michigan , 930 N. University Avenue, Ann Arbor, Michigan 48109-1055, United States.
authors.forename: Nicholas R
authors.initials: NR
authors.lastname: Babij
authors.forename: Grace M
authors.initials: GM
authors.lastname: McKenna
authors.forename: Ryan M
authors.initials: RM
authors.lastname: Fornwald
authors.forename: John P
authors.initials: JP
authors.lastname: Wolfe
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000475:Alkenes; D011759:Pyrrolidines; D013449:Sulfonamides; D010165:Palladium