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Regioselectivity and Diastereoselectivity in the 1,3-Dipolar Cycloadditions of Nitrones with Acrylonitrile and Maleonitrile. The Origin of ENDO/EXO Selectivity^#

Augusto Rastelli*; Remo Gandolfi**; Mirko Sarzi Amadè** ^(*) Dipartimento di Chimica, Università di Modena, 183 Via Campi, 41100 Modena, Italy.^(**) Dipartimento di Chimica Organica, Università di Pavia, 10 V.le Taramelli, 27100 Pavia, Italy

1 Introduction

The nitrone functionality is a 4-π-electron system capable of undergoing reactions with other multiply bonded systems in a process, the 1,3-dipolar cycloaddition, not unlike the Diels-Alder reaction. The foreseen potentiality of nitrone cycloadditions¹ has been largely confirmed in the last thirty years so that such reactions are now ...

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