VICINAL OXYAMINATION

OSMIUM-CATALYZED VICINAL OXYAMINATION OF OLEFINS BY CHLORAMINE-T cis-2-(p-TOLUENESULFONAMIDO)CYCLOHEXANOL AND 2-METHYL-3-(p-TOLUENESULFONAMIDO)-2-PENTANOL... [Pg.132]

OSMIUM-CATALYZED VICINAL OXYAMINATION OF OLEFINS BY JV-CHLORO-A-ARGENTOCARBAMATES ETHYL threo-l 1 (2-HYDROX Y-l, 2-DIPHENYI,-ETHYL)]CARBAMATE... [Pg.136]

OSMIUM-CATALYZED VICINAL OXYAMINATION OF OLEFINS BY Af-CHLORO-jV-ARGENTOCARBAMATES ETHYL fArco-[l-(2.HYDROXY-l,2-DIPHENYL-ETHYDICARBAMATE... [Pg.93]

Sharpless and coworkers have reported a new series of reagents for allylic amination of olefins,79-5 vicinal oxyamination of olefins,76 and 1,2-diamination of 1,3-dienes.77... [Pg.273]

Oxyanunation. Vicinal oxyamination of olefins can be carried out with OSO4 in catalytic amounts with this N-chloro-N-argentocarbamate (c/. Osmium tetroxide-Chloramine-T, 7, 256). A major improvement over chloroamine-T is that the —COOCfCHaja group is readily eliminated. [Pg.492]

Vicinal oxyamination. In the presence of catalytic amounts (1%) of osmium tetroxide the trihydrate of chloramine-T reacts with alkanes to form vicinal hydroxy />-toluenesulfonamides (equation I). The effective reagent is considered to be (1). In some instances addition of silver nitrate was found to be advantageous. ... [Pg.132]

Oxyamination of Alkenes and Oxidation of Other Functional Groups. Osmium tetroxide catalyzes the vicinal oxyamination of alkenes to give c/s-vicinal hydroxyamides with Chloramine-T (eq 23) and alkyl Ai-chloro-M-argentocarbamate, generated in situ by the reaction of alkyl Ai-chlorosodiocarbamate (such as ethyl or f-butyl iV-chlorosodiocarbamate) with Silver(I) Nitrate (eq 24). ... [Pg.267]

Improved procedures for osmium-catalysed vicinal oxyamination of olefins by JV-chlorosodiocarbamates-Hg(N03)2-Et4NOAc are recommended especially for trisubstituted systems. Asymmetric induction in the reaction of OSO4 with olefins using dihydroquinidine acetate in up to 83% e.e. is now possible. "... [Pg.210]

Following the report last year of the first vicinal oxyamination of olefins using aminated derivatives of osmium tetroxide. Sharpless has extended this analogy to oxidations involving selenium dioxide. Two aza analogues of selenium dioxide have been prepared by either the reaction of selenium tetrachloride with the amine or... [Pg.21]

Diphenyl sulphide reacts with anhydrous chloramine-T to give an adduct (8), which is a useful reagent for the amination of olefins (Scheme 7). The osmium-catalysed oxyamination of olefins by chloramine-T has been improved by phase-transfer catalysis, and the stereospecific vicinal oxyamination of olefins by alkylimido-osmium compounds has been reported. ... [Pg.166]

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