The Reaction of α-Diazo-β-hydroxy Esters with Boron Trifluoride Etherate: Generation and Rearrangement of Destabilized Vinyl Cations. A Detailed Experimental and …

…, B Natalini, BM Sadeghpour, M Marinozzi…

Index: Pellicciari, Roberto; Natalini, Benedetto; Sadeghpour, Bahman M.; Marinozzi, Maura; Snyder, James P.; Williamson, Bobby L.; Kuethe, Jeffrey T.; Padwa, Albert Journal of the American Chemical Society, 1996 , vol. 118, # 1 p. 1 - 12

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Citation Number: 62

Abstract

Cyclic ethyl 2-diazo-3-hydroxy carboxylates were prepared by treating ethyl diazoacetate with LDA followed by reaction with a series of cyclic ketones. Further treatment of these α- diazo-β-hydroxy esters with boron trifluoride etherate in various solvents affords an unusual array of products. Product types and ratios were found to be strongly dependent on ring size and the solvent used. The reaction proceeds by Lewis acid complexation of the alcohol ...