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ChemInform Abstract: Photochemical Rearrangement of 2-Phenylthio-3-aminocyclohexanols. New Access to Deoxyazasugars and Their Derivatives.

✍ Scribed by D. GRAVEL; A. AMOOZADEH; Y. WANG


Publisher
John Wiley and Sons
Year
2010
Weight
29 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis


Photochemical

Rearrangement of 2-Phenylthio-3aminocyclohexanols.

New Access to Deoxyazasugars and Their Derivatives.

-Photoinduced regioselective rearrangement of carbocyclic 2-phenylthio amino alcohol (I) leads to the formation of deoxyazasugar (II). Under acidic dehydration conditions the dehydropiperidine derivative (III) is formed. Further transformations of (II) and (III) provide access to variously substituted derivatives such as the piperidine (IV) and the ring-opened aminosulfoxides (V) and (VI). -(GRAVEL, D.


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