title: Enantioselective Aza-Sakurai Cyclizations: Dual Role of Thiourea as H-Bond Donor and Lewis Base.
abstract: An enantioselective, catalytic aza-Sakurai cyclization of chlorolactams has been developed as an efficient entry into indolizidine and quinolizidine frameworks. Structure-enantioselectivity relationship studies and mechanistic analysis point to a dual role of the catalyst wherein the thiourea moiety of the catalyst is engaged in both anion binding and Lewis base activation of a substrate.
authors: Department of Chemistry and Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States.
authors: Yongho
authors: Y
authors: Park
authors: Department of Chemistry and Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States.
authors: Corinna S
authors: CS
authors: Schindler
authors: Department of Chemistry and Chemical Biology, Harvard University , Cambridge, Massachusetts 02138, United States.
authors: Eric N
authors: EN
authors: Jacobsen
mesh_terms: D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D006860:Hydrogen Bonding; D007769:Lactams / Q000737:chemistry*; D058115:Lewis Bases / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001372:Aza Compounds; D007769:Lactams; D058115:Lewis Bases