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

R Annunziata, M Benaglia, M Cinquini…

文献索引: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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被引用次数: 63

摘要

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 ...