Enolate Claisen rearrangement of esters from furanoid and pyranoid glycals

…, S Thaisrivongs, N Vanier, CS Wilcox

Index: Ireland, Robert E.; Thaisrivongs, Suvit; Vanier, Noel; Wilcox, C. S. Journal of Organic Chemistry, 1980 , vol. 45, # 1 p. 48 - 61

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Citation Number: 176

Abstract

A general method is described for the formation of furanoid and pyranoid glycals. Thus, lithium-ammonia reduction of the corresponding l-chloro-2, 3-0-isopropylidene furanoid and pyranoid carbohydrate derivatives affords the desired glycals in 87-92% yields. Several examples that reveal the scope of this process are described. The formation of C-glycosides from the glycal esters through application of the ester enolate Claisen rearrangement is ...