title: Enantioselective synthesis of anti-beta-substituted gamma,delta-unsaturated amino acids: a highly selective asymmetric thio-Claisen rearrangement.
abstract: A novel synthesis of optically active anti-beta-substituted gamma,delta-unsaturated amino acids via a thio-Claisen rearrangement has been achieved. A 2,5-diphenylpyrrolidine was used as a C2-symmetric chiral auxiliary to control the stereochemistry, giving good yields and excellent diastereoselectivities and enantioselectivities.
authors.affiliation: Department of Chemistry, University of Arizona, Tucson, Arizona 85721, USA.
authors.forename: Zhihua
authors.initials: Z
authors.lastname: Liu
authors.forename: Hongchang
authors.initials: H
authors.lastname: Qu
authors.forename: Xuyuan
authors.initials: X
authors.lastname: Gu
authors.forename: Byoung J
authors.initials: BJ
authors.lastname: Min
authors.forename: Gary S
authors.initials: GS
authors.lastname: Nichol
authors.forename: Joel
authors.initials: J
authors.lastname: Nyberg
authors.forename: Victor J
authors.initials: VJ
authors.lastname: Hruby
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity; D013455:Sulfur / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D013455:Sulfur