title: A facile Cu(I)/TF-BiphamPhos-catalyzed asymmetric approach to unnatural α-amino acid derivatives containing gem-bisphosphonates.
abstract: A novel catalytic asymmetric Michael addition of azomethine ylide with β-substituted alkylidene bisphosphates was realized in the presence of a chiral copper(I)/TF-BiphamPhos complex. The present system provides a unique and facile access to enantioenriched unnatural α-amino acid derivatives containing gem-bisphosphonates (gem-BPs) in high yields with excellent diastereoselectivities and enantioselectivities. Subsequent transformations lead to the expedient preparation of biologically active unnatural α-amino acid derivatives containing BPs and bisphosphonic acids without loss of diastereo- and enantiomeric excess.
authors.affiliation: College of Chemistry and Molecular Sciences, Wuhan University, Wuhan 430072, China.
authors.forename: Zhi-Yong
authors.initials: ZY
authors.lastname: Xue
authors.forename: Qing-Hua
authors.initials: QH
authors.lastname: Li
authors.forename: Hai-Yan
authors.initials: HY
authors.lastname: Tao
authors.forename: Chun-Jiang
authors.initials: CJ
authors.lastname: Wang
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry*; D003300:Copper / Q000737:chemistry*; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry*; D063065:Organophosphonates / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D056831:Coordination Complexes; D009942:Organometallic Compounds; D063065:Organophosphonates; C549499:TF-BiphamPhos; D003300:Copper