title: Enantioselective synthesis of Amaryllidaceae alkaloids (+)-vittatine, (+)-epi-vittatine, and (+)-buphanisine.
abstract: Cat. on a hot tin roof: Enantioselective catalytic Michael addition of α-cyanoketones to acrylates under bifunctional organocatalysis was used to construct the unique arylic all-carbon quaternary stereocenter, which is synthetically crucial in the chemical synthesis of optically pure cis-aryl hydroindole alkaloids. The protocol offers an asymmetric route to (+)-vittatine, (+)-epi-vittatine, and (+)-buphanisine.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, 222 Tianshui Nanlu, Lanzhou 730000, China.
authors.forename: Meng-Xue
authors.initials: MX
authors.lastname: Wei
authors.forename: Cheng-Tao
authors.initials: CT
authors.lastname: Wang
authors.forename: Ji-Yuan
authors.initials: JY
authors.lastname: Du
authors.forename: Hu
authors.initials: H
authors.lastname: Qu
authors.forename: Pei-Rong
authors.initials: PR
authors.lastname: Yin
authors.forename: Xu
authors.initials: X
authors.lastname: Bao
authors.forename: Xiao-Yan
authors.initials: XY
authors.lastname: Ma
authors.forename: Xian-He
authors.initials: XH
authors.lastname: Zhao
authors.forename: Guo-Biao
authors.initials: GB
authors.lastname: Zhang
authors.forename: Chun-An
authors.initials: CA
authors.lastname: Fan
mesh_terms: D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D019668:Liliaceae / Q000737:chemistry*; D008968:Molecular Conformation; D010617:Phenanthridines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D047151:Amaryllidaceae Alkaloids; D010617:Phenanthridines; C488939:vittatine 1
keywords: Michael addition; alkaloids; asymmetric synthesis; organocatalysis; quaternary carbon