Tetrahedron

Direct carbohydrate to carbocycle conversions via intramolecular allylation with Et 2 Zn/Pd (0)

JM Aurrecoechea, M Arrate, JH Gil, B López

Index: Aurrecoechea, Jose M.; Arrate, Monica; Gil, Jesus H.; Lopez, Beatriz Tetrahedron, 2003 , vol. 59, # 29 p. 5515 - 5522

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Citation Number: 12

Abstract

Treatment of 5-vinylpyranosides with Et2Zn and catalytic Pd (0), in the presence of ZnCl2, results in the formation of 5-membered carbocyclic products. This carbohydrate ring- contraction features an intramolecular allylation of a ring-opened carbohydrate aldehyde by an in situ-generated nucleophilic allylzinc species. The stereoselectivity about vinyl and free hydroxyl groups at the newly created stereogenic centers varies from low to moderate ...

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