Regio-and stereoselectivity of captodative olefins in 1, 3-dipolar cycloadditions. A DFT/HSAB theory rationale for the observed regiochemistry of nitrones

…, F Méndez, HA Jiménez-Vázquez…

Index: Herrera; Nagarajan; Morales; Mendez; Jimenez-Vazquez; Zepeda; Tamariz Journal of Organic Chemistry, 2001 , vol. 66, # 4 p. 1252 - 1263

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Citation Number: 68

Abstract

Captodative olefins 1-acetylvinyl carboxylates proved to be highly regioselective dipolarophiles in 1, 3-dipolar cycloadditon to propionitrile oxide, arylphenylnitrile imines, diazoalkanes, and nitrones to yield the corresponding 5-substituted heterocycles. The addition of the latter was also stereoselective, being slightly susceptible to steric demand of the carboxylate substituent in the olefin. All atempts to cleave the isoxazolidine NO bond ...