Reaction of phosphorus trichloride with propylene sulfide

Conclusions The reaction of phosphorus trichloride with propylene sulfide was studied.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 7, pp. 1255–1256, July, 1966.     

Reaction of phosphorus trichloride with carboxylic acids

The reaction of phosphorus trichloride with a number of monobasic carboxylic acids has been studied and the optimum ratio of reactants for the yield of acid chlorides has been established. Based on analysis and the data from³¹P NMR spectroscopy of the phosphorus-containing products from this reaction it is shown that at 402-50°C a mixture of P-H acids having a predominant content of pyrophosphorous acid is formed.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 428–432, February, 1990.     

Palladium-catalyzed synthesis of novel optically active tryptophan analogues

[reaction: see text] Both unsaturated proline derivatives and optically active tryptophan analogues have been obtained via Pd-catalyzed cyclization of aniline-containing acetylenic amino acids. The side chain length of the cyclization precursor determines which one of the two possible products will be formed.     

Reaction of oxetanes with phosphorus trichloride and alkyldichlorophosphines

Conclusions Reactions of phosphorus trichloride or alkyldichlorophosphines with 3,3-dimethyloxetane or 2-methyl-oxetane yields (alkyl),-dimethyl--chloropropyl phosphorous acid (di)chlorides or (alkyl)-methyl--chloropropyl phosphorous acid (di)chlorides respectively.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1426–1428, June, 1970.     

A new strategy for the synthesis of optically active benzylic fluorides and corresponding five-membered heteroaromatic analogues

Benzylic fluorides, as well as five-membered heterocycles, have been obtained in high ee’s through cycloaddition reactions starting from easily accessible optically active propargylic fluorides.     

A new synthesis of optically active α-alanine

Summary Optically active -alanine has been synthesized from pyruvic acid using N-aminoanabasine as the asymmetrizing agent.     

A new convenient route to enantiopure 2-coumarinyloxypropanals: application to the synthesis of optically active geiparvarin analogues

A new convenient route to enantiopure 2-coumarinyloxypropanals is described: Rosenmund reduction of (R)- or (S)-2-coumarinyloxypropanoyl chlorides afforded in good yields the corresponding 2-coumarinyloxypropanals. Their subsequent aldolic condensation with 3(2H)-furanones, followed by dehydration, led to enantiopure geiparvarin analogues now being investigated as promising antitumoral compounds.     

Reaction of sulphoximides with diazomalonate in the presence of Cu-salt : A new synthesis and stereochemistry of optically active oxosulphonium ylides

Sulphoximides (Ia–Ie) were found to react with dimethyl diazomalonate (DDM) in the presence of a catalytic amount of Cu-salts affording the corresponding oxosulphonium ylides in moderate yields. The reaction did not proceed at all under irradiation of UV light. (?)-Methylphenyloxosulphonium bis(methoxycarbonyl)-methylide ((?)-IIb) was obtained from (+)-(S)-methylphenylsulphoximide ((+)-(S)-Ib) together with (?)-(S)-methyl phenyl sulphoxide ((?)-(S)-IIIb) by this reaction. Hydrolysis of (?)-IIb gave (+)-methylphenyloxosulphonium methoxycarbonylmethylide ((+)-IIf) which was converted to (?)-(S)-IIIb upon treatment with dibenzoylethylene. Stereochemical cycle starting from (+)-(S)-Ib to (?)-(S)-IIIb was established and the absolute configurations of both ylides, (?)-IIb and (+)-IIf were assigned as (R)-configuration. The stereochemical courses, namely from (+)-(S)-Ib or (?)-(S)-IIIb to (?)-(R)-IIb or (+)-(R)-IIf to (?)-(S)-IIIb were determined as retention processes. The optical purities of the oxosulphonium ylides obtained from both reactions, (+)-(S)-Ib→(?)-(R)-IIb and (?)-(S)-IIIb→(?)-(R)-IIb, were almost equal. These results indicate that the mechanism of the reaction of sulphoximides with carbenes (or carbenoids) involves the initial formation of the sulphoxides which react subsequently with carbenes to afford the final products.     

Asymmetric synthesis of new optically active sulfinamides of menthane series and their derivatives

Asymmetric syntheses were performed of neomenthanesulfinamide in the yield of 60% and de 74%, of neomenthanesulfinaldimines and N-substituted neomenthanesulfinamides in 22–80 and 40–90% yields respectively.     

Reaction of guanosine derivatives with phosphorus trichloride in acetone

2′, 3′-Di-O-protected guanosine derivatives (Ia and Ib) were allowed to react with phosphorus trichloride in acetone to give the N²-(1-methyl-1-phosphono)ethylguanosine derivatives (IIIa and IIIb).     

A new synthesis of atanine,khaplofoline and their analogues

A facile synthesis of Atanine, Khaplofoline and their analogues is described. The method involves condensation of an appropriately substituted 2-quinolone-3-acetic acid with isobutryaldehyde, as the starting point.