Nagao, Yoshimitsu published the artcileUtilization 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, Related Products of chlorides-buliding-blocks, the publication is Journal of Organic Chemistry (1985), 50(21), 4072-80, database is CAplus.
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.
Journal of Organic Chemistry published new progress about 5034-06-0. 5034-06-0 belongs to chlorides-buliding-blocks, auxiliary class Salt,Aliphatic hydrocarbon chain, name is trimethyloxosulphonium chloride, and the molecular formula is C3H9ClOS, Related Products of chlorides-buliding-blocks.
Referemce:
https://en.wikipedia.org/wiki/Chloride,
Chlorides – an overview | ScienceDirect Topics