title: One-Pot Dichotomous Construction of Inside-Azayohimban and Pro-Azayohimban Systems via an Enantioselective Organocatalytic Cascade; Their Use as a Model to Probe the (Aza-)Indole Local Solvent Environment.
abstract: A one-pot enantioselective synthesis of 7-azaindole-octahydroisoquinolin-3-one and an inside-aza-yohimbane system containing five contiguous stereogenic centers with high enantioselectivities (>99% ee) was achieved. The prepared highly functionalized polycyclic system provides a model for probing the solvent catalyzed proton transfer reaction and mimicking the local environment of the tryptophan moiety in proteins.
authors.affiliation: Department of Chemistry and Biochemistry, National Chung Cheng University , Chia-Yi, 621, Taiwan, R.O.C.
authors.forename: Van-Wei
authors.initials: VW
authors.lastname: Yang
authors.affiliation: Department of Chemistry and Biochemistry, National Chung Cheng University , Chia-Yi, 621, Taiwan, R.O.C.
authors.forename: Bor-Cherng
authors.initials: BC
authors.lastname: Hong
authors.affiliation: Department of Chemistry and Biochemistry, National Chung Cheng University , Chia-Yi, 621, Taiwan, R.O.C.
authors.forename: Hsin-Kai
authors.initials: HK
authors.lastname: Kao
authors.affiliation: Department of Chemistry, National Taiwan University , Taipei, 106, Taiwan, R.O.C.
authors.forename: Ting-Hsun
authors.initials: TH
authors.lastname: Tu
authors.affiliation: Department of Chemistry, National Taiwan University , Taipei, 106, Taiwan, R.O.C.
authors.forename: Jiun-Yi
authors.initials: JY
authors.lastname: Shen
authors.affiliation: Department of Chemistry, National Taiwan University , Taipei, 106, Taiwan, R.O.C.
authors.forename: Chi-Lin
authors.initials: CL
authors.lastname: Chen
authors.affiliation: Department of Chemistry, National Taiwan University , Taipei, 106, Taiwan, R.O.C.
authors.forename: Gene-Hsiang
authors.initials: GH
authors.lastname: Lee
authors.affiliation: Department of Chemistry, National Taiwan University , Taipei, 106, Taiwan, R.O.C.
authors.forename: Pi-Tai
authors.initials: PT
authors.lastname: Chou
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D015394:Molecular Structure; D011506:Proteins / Q000737:chemistry; D012997:Solvents; D013237:Stereoisomerism; D014364:Tryptophan / Q000737:chemistry
chemical_list: C000606233:7-azaindole-octahydroisoquinolin-3-one; D007211:Indoles; D007546:Isoquinolines; D011506:Proteins; D012997:Solvents; D014364:Tryptophan