title: Efficient asymmetric synthesis of N-protected-β-aryloxyamino acids via regioselective ring opening of serine sulfamidate carboxylic acid.
abstract: First regioselective ring opening of serine derived cyclic sulfamidate by hard nucleophiles like ArONa is developed, where β-elimination of serine sulfamidate ester by stronger nucleophiles is overcome by reversal of the electronic effect of the carboxylate anion. This method provides easy and direct access to a variety of N-Boc- and N-PMB protected β-aryloxy-α-amino acids with complete retention of enantiopurity in moderate to high yields.
authors.affiliation: Department of Chemistry, Guru Jambheshwar University of Science and Technology, Hisar, Haryana 125001, India.
authors.forename: Rajesh
authors.initials: R
authors.lastname: Malhotra
authors.forename: Tushar K
authors.initials: TK
authors.lastname: Dey
authors.forename: Swarup
authors.initials: S
authors.lastname: Dutta
authors.forename: Sourav
authors.initials: S
authors.lastname: Basu
authors.forename: Saumen
authors.initials: S
authors.lastname: Hajra
mesh_terms: D000577:Amides / Q000737:chemistry*; D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002264:Carboxylic Acids / Q000737:chemistry*; D015394:Molecular Structure; D012694:Serine / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000577:Amides; D000596:Amino Acids; D002264:Carboxylic Acids; D012694:Serine