チアゾリジンの研究(第2報) : ラセミ-2-アミノ-アルカンチオールの光学分割について

抄録

The condensation product of DL-trans-2-aminocyclohexanethiol (Irac.) and D-glucose was fractionated into a pair of diastereomers (IIa and IIb) by recrystalization from ethanol. On treatment with cyclohexanone, IIa and IIb were derived into (+)-trans-perhydrocyclohexa [d]-thiazole-2-spiro-1'-cyclohexane (IIId) and the (-) antipode (IIIe) respectively, expelling D-glucose. IIId and IIIe were easily hydrolyzed in hydrochloric acid solution to give (-)-trans-2-aminocyclohexanethiol (Ie) and the (+) antipode (Id) respectively, with inversion of the sign. This procedure provides a new method for optical resolution of resolvable 2-aminoalkanethiol.