title: Enantiopure synthesis of dihydrobenzo[1,4]-oxazine-3-carboxylic acids and a route to benzoxazinyl oxazolidinones.
abstract: A two step protocol is developed for the efficient synthesis of enantiopure N-Boc-dihydrobenzo[b]-1,4-oxazine-3-carboxylic acids 4 from serine derived cyclic sulfamidate via intramolecular arylamination. The RuPhos Palladacycle along with additional RuPhos ligand is found to be an efficient catalyst for the arylamination of β-(2-bromoaryloxy)amino acids 3 to provide easy and direct access to a variety of dihydrobenzo[b]-1,4-oxazine-3-carboxylic acids 4 with complete retention of enantiopurity in moderate to high yields. Dihydrobenzo[b]-1,4-oxazine-3-carboxylic acids are not only important unnatural amino acids, but are key precursors for the synthesis of important compounds such as benzoxazinyl oxazolidinones. A general approach for the synthesis of benzoxazinyl oxazolidinone is presented.
authors: Department of Chemistry, Guru Jambheshwar University of Science and Technology, Hisar, Haryana 125001, India.
authors: Rajesh
authors: R
authors: Malhotra
authors: Tushar K
authors: TK
authors: Dey
authors: Sourav
authors: S
authors: Basu
authors: Saumen
authors: S
authors: Hajra
mesh_terms: D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D010078:Oxazines / Q000138:chemical synthesis* / Q000737:chemistry; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D002264:Carboxylic Acids; D010078:Oxazines; D023303:Oxazolidinones