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Efficient 1,4-asymmetric induction with an enantiopure aminoalkyl group as the chiral auxiliary has been achieved in the first example of diastereoselective alkylation (up to 98:2) of a sulfenate anion, readily prepared by oxidation of the corresponding thiolate. The stereochemistry of the sulfoxide produced is the opposite of that obtained by the conventional route based on oxidation of the sulfide precursor.

The first efficient and general method for the generation of sulfinate anions by oxidation of the corresponding thiolates is described. The oxidizing agent employed is the classical 2-(phenylsulfonyl)-3-phenyloxaziridine, commonly known as the Davis reagent. Subsequent S-alkylation of the sulfinates under phase-transfer catalysis affords sulfones 6 in 71−91% isolated yields (10 examples).

d-Mannofuranosyl-ethanethioamides were prepared in good yields viaa Horner-Wadsworth-Emmons reaction of thiocarbamoylmethylphosphonates with 2,3:5,6-di-O-isopropylidene-α-d-mannofuranose. New glycosyl-ethanethioamides were obtained and one of them was converted into the corresponding dithioester which is a potential sugar substituted thioacylating agent for aminoacids.

Oxaziridine-mediated oxidation reactions of thiolates into sulfenates and sulfinates are reported.

Oxaziridine-mediated oxidation reactions of thiolates into sulfenates and sulfinates are reported.

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ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.

ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.