1, 3-Dipolar Cycloadditions to Baylis-Hillman Adducts: Rationale for the Observed Diastereoselectivity

R Annunziata, M Benaglia, M Cinquini…

Index: Annunziata, Rita; Benaglia, Maurizio; Cinquini, Mauro; Cozzi, Franco; Raimondi, Laura Journal of Organic Chemistry, 1995 , vol. 60, # 15 p. 4697 - 4706

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Citation Number: 63

Abstract

Diazomethane and benzonitrile oxide cycloadditions were performed on Baylis-Hillman adducts derived from methyl acrylate and aldehydes (/?'-alkoxy-a, P-unsaturated esters). The reactions proceed in good chemical yields, and their stereochemical outcome can be explained by the “inside alkoxy effect” theory. In the case of diazomethane cycloadditions, however, electrostatic factors play a reduced role in comparison to the corresponding ...