On October 18, 1985, Nagao, Yoshimitsu; Ikeda, Takao; Inoue, Takehisa; Yagi, Masahiro; Shiro, Motoo; Fujita, Eiichi published an article.Reference of trimethyloxosulphonium chloride The title of the article was Utilization of sulfur-containing leaving group. 7. Highly selective nonenzymic chiral induction into 3-methylglutaric acid and cis-4-cyclohexen-1,2-ylenebis(acetic acid) utilizing a functional five-membered heterocycle 4(R)-MCTT. And the article contained the following:
Diamide I, prepared by treatment of 3-methylglutaric acid with 4(R)-(methoxycarbonyl)-1,3-thiazolidine-2-thione [4(R)-MCTT] in the presence of DCC in pyridine, was subjected to aminolysis with 1 equiv of piperidine in CH2Cl2 at -30° to give a mixture of diastereomers II [R2N = piperidino, R12N = MCTT moiety (III)] and II (R2N = MCTT moiety, R12N = piperidino) in a 88:12 ratio. III was separated by silica gel column chromatog. and treated with various nucleophiles to give optically pure bifunctional synthons (II; R2N and R12N = nucleophilic group) in high yields. Highly selective chiral induction into cis-4-cyclohexen-1,2-ylenebis(acetic acid) was also performed. Aminolysis of IV (R2N and R12N = MCTT moiety) (V) with 1 equiv of piperidine gave 94% diastereomer IV (R2N = piperidino, R12N = MCTT moiety). Similar chiral induction into cis-cyclohexan-1,2-xylenebis(acetic acid) and aminolysis of its 4(R)-MCTT diamide (VI) with piperidine were also carried out; opposite selectivity was obtained. The conformations of V and VI in a solvent, the relationship between the susceptibility of their conformations and environmental temperature, and the diastereoselectivity of the reaction are discussed on the basis of the 400-MHz 1H NMR spectra. The experimental process involved the reaction of trimethyloxosulphonium chloride(cas: 5034-06-0).Reference of trimethyloxosulphonium chloride
The Article related to chiral induction methylglutaric cyclohexenebisacetic acid, thiazolidinethionecarboxylate amidation methylglutaric cyclohexenebisacetic acid, conformation thiazolidinethionecarboxylate diamide, aminolysis thiazolidinethionecarboxylate diamide stereochem and other aspects.Reference of trimethyloxosulphonium chloride
Referemce:
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics