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ChemInform Abstract: Differential Oxidation of Endocyclic Enecarbamates. Synthesis of Cyclic β-Hydroxy-α-amino Acids.

✍ Scribed by C. H. SUGISAKI; P. J. CARROLL; C. R. D. CORREIA

Publisher
John Wiley and Sons
Year
2010
Weight
34 KB
Volume
29
Category
Article
ISSN
0931-7597

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✦ Synopsis

Differential Oxidation of Endocyclic Enecarbamates. Synthesis of Cyclic β-Hydroxy-α-amino Acids.

-Oxidation of five-and six-membered endocyclic enecarbamates (I) employing MCPBA and dimethyldioxirane (DMD) as oxidants is investigated. In the presence of methanol as nucleophile, β-hydroxy-α-methoxypyrrolidines and piperidines (III) are obtained.

Acylation of the primary DMD-oxidation product followed by nucleophilic displacement with cyanide yields α-cyano-β-acetoxy pyrrolidine (VI). Furthermore, application of dihydroxylation conditions allows an entry to diols such as (VIII). -(SUGISAKI, C.

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