Enantiopure synthesis of dihydrobenzo[1, 4]-oxazine-3-carboxylic acids and a route to benzoxazinyl oxazolidinones. Issue 11 (3rd February 2015)

• Record Type: Journal Article
• Authors: Malhotra, Rajesh; Dey, Tushar K.; Basu, Sourav; Hajra, Saumen
• Is Part Of: Organic & biomolecular chemistry. Volume 13:Issue 11(2015)
• Page Start: 3211
• Page End: 3219
• Publication Date: 2015-02-03
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c4ob02475c
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A two step protocol is developed for the enantiopure synthesis of dihydrobenzoxazine-3-carboxylic acids via RuPhos Palladacycle-catalyzed aminoarylation of β-(2-bromoaryloxy)amino acids. Abstract : A two step protocol is developed for the efficient synthesis of enantiopure N -Boc-dihydrobenzo[ b ]-1, 4-oxazine-3-carboxylic acids4 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 acids3 to provide easy and direct access to a variety of dihydrobenzo[ b ]-1, 4-oxazine-3-carboxylic acids4 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.