title: Catalytic asymmetric 1,2-addition of α-isothiocyanato phosphonates: synthesis of chiral β-hydroxy- or β-amino-substituted α-amino phosphonic acid derivatives.
abstract: α-Amino phosphonic acid derivatives are considered to be the most important structural analogues of α-amino acids and have a very wide range of applications. However, approaches for the catalytic asymmetric synthesis of such useful compounds are very limited. In this work, simple, efficient, and versatile organocatalytic asymmetric 1,2-addition reactions of α-isothiocyanato phosphonate were developed. Through these processes, derivatives of β-hydroxy-α-amino phosphonic acid and α,β-diamino phosphonic acid, as well as highly functionalized phosphonate-substituted spirooxindole, can be efficiently constructed (up to 99 % yield, d.r. >20:1, and >99 % ee). This novel method provides a new route for the enantioselective functionalization of α-phosphonic acid derivatives.
authors.affiliation: Key Laboratory of Preclinical Study for New Drugs of Gansu Province, School of Basic Medical Sciences, Lanzhou University, Lanzhou, 730000 (China).
authors.forename: Yi-Ming
authors.initials: YM
authors.lastname: Cao
authors.forename: Fang-Fang
authors.initials: FF
authors.lastname: Shen
authors.forename: Fu-Ting
authors.initials: FT
authors.lastname: Zhang
authors.forename: Jin-Long
authors.initials: JL
authors.lastname: Zhang
authors.forename: Rui
authors.initials: R
authors.lastname: Wang
mesh_terms: D002384:Catalysis; D003485:Cyanates / Q000737:chemistry; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry*; D010757:Phosphorous Acids / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D003485:Cyanates; D063065:Organophosphonates; D010757:Phosphorous Acids; C570063:phosphonic acid
keywords: asymmetric synthesis; organocatalysis; synthetic methods; α-amino phosphonic acids; α-isothiocyanato compounds