@article{oai:nagasaki-u.repo.nii.ac.jp:00007657, author = {Oba, Makoto and Shimabukuro, Atsushi and Ono, Miyako and Doi, Mitsunobu and Tanaka, Masakazu}, issue = {8}, journal = {Tetrahedron: Asymmetry}, month = {Apr}, note = {A method of synthesizing an optically active cyclic methionine analogue, 3-aminotetrahydrothiophene-3-carboxylic acid (At5c), is described. A Bucherer-Bergs reaction of 4,5-dihydro-3(2H)-thiophenone and the subsequent alkaline hydrolysis of a hydantoin, followed by Cbz protection of the amine, afforded racemic Cbz-At5c (±)-3 in excellent yield. Diastereomeric esters derived from Cbz-At5c (±)-3 and (R)-BINOL could be separated by column chromatography to give both diastereomers with >99% de. X-ray crystallographic analysis revealed the absolute configuration of the synthesized amino acid derived from the less polar diastereomeric ester to be (S)., Tetrahedron: Asymmetry, 24(8), pp.464-467; 2013}, pages = {464--467}, title = {Synthesis of both enantiomers of cyclic methionine analogue: (R)- and (S)-3-aminotetrahydrothiophene-3-carboxylic acids}, volume = {24}, year = {2013} }