title: Highly diastereo- and enantioselective synthesis of syn-β-substituted tryptophans via asymmetric Michael addition of a chiral equivalent of nucleophilic glycine and sulfonylindoles.
abstract: The asymmetric synthesis of syn-β-substituted tryptophan derivatives was carried out by the Michael addition of chiral equivalent of nucleophilic glycine with sulfonylindoles, and high diastereo- and enantioselectivities were achieved. The resulting adducts were readily converted to syn-β-substituted tryptophans in 96% yield, indicating that the proposed method is a highly efficient route to chiral syn-β-substituted tryptophans.
authors.affiliation: State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Shanghai, PR China.
authors.forename: Jiang
authors.initials: J
authors.lastname: Wang
authors.forename: Shengbin
authors.initials: S
authors.lastname: Zhou
authors.forename: Daizong
authors.initials: D
authors.lastname: Lin
authors.forename: Xiao
authors.initials: X
authors.lastname: Ding
authors.forename: Hualiang
authors.initials: H
authors.lastname: Jiang
authors.forename: Hong
authors.initials: H
authors.lastname: Liu
mesh_terms: D056831:Coordination Complexes / Q000737:chemistry; D005998:Glycine / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D009532:Nickel / Q000737:chemistry; D012545:Schiff Bases / Q000737:chemistry; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry; D014364:Tryptophan / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D056831:Coordination Complexes; D007211:Indoles; D012545:Schiff Bases; D013450:Sulfones; D009532:Nickel; C030374:indole; D014364:Tryptophan; D005998:Glycine