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ChemInform Abstract: Synthesis of 2-Vinylcyclopentanols by SmI2/Pd(0)-Promoted Carbohydrate Ring-Contraction.

✍ Scribed by J. M. AURRECOECHEA; B. LOPEZ

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

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✦ Synopsis

Synthesis of 2-Vinylcyclopentanols by SmI 2 /Pd(0)-Promoted Carbohydrate Ring-Contraction.

-Treatment of methyl 5-vinylpyranosides such as (I) with SmI 2 in the presence of catalytic Pd(0) results in ring contraction and direct transformation of the carbohydrate structure into functionalized carbocycles. The diastereoselectivity of the reaction is moderate; however, a preference for the trans-relationship between the newly created stereocenters is observed. -(AURRECOECHEA,

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