title: Highly torquoselective electrocyclizations and competing 1,7-hydrogen shifts of 1-azatrienes with silyl substitution at the allylic carbon.
abstract: Highly torquoselective electrocyclizations of chiral 1-azatrienes are described. These 1-azatrienes contain an allylic stereocenter that is substituted with a silyl group and are derived in situ from condensation of γ-silyl-substituted enals with vinylogous amides. The ensuing stereoselective ring closures are part of a tandem sequence that constitutes an aza-[3 + 3] annulation method for constructing 1,2-dihydropyridines. Several mechanisms for the formal 1,7-hydrogen shift of these 1-azatrienes were evaluated computationally.
authors: †Division of Pharmaceutical Sciences, School of Pharmacy, and Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53705, United States.
authors: Zhi-Xiong
authors: ZX
authors: Ma
authors: ‡Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
authors: Ashay
authors: A
authors: Patel
authors: ‡Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States.
authors: K N
authors: KN
authors: Houk
authors: †Division of Pharmaceutical Sciences, School of Pharmacy, and Department of Chemistry, University of Wisconsin, Madison, Wisconsin 53705, United States.
authors: Richard P
authors: RP
authors: Hsung
mesh_terms: D001372:Aza Compounds / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006859:Hydrogen / Q000737:chemistry; D017646:Organosilicon Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001372:Aza Compounds; D017646:Organosilicon Compounds; D002244:Carbon; D006859:Hydrogen