Intra-and intermolecular 1, 3-dipolar cycloaddition of sugar ketonitrones with mono-, di-, and trisubstituted dipolarophiles

S Torrente, B Noya, V Branchadell…

Index: Torrente, Susana; Noya, Beatriz; Branchadell, Vicenc; Alonso, Ricardo Journal of Organic Chemistry, 2003 , vol. 68, # 12 p. 4772 - 4783

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Citation Number: 29

Abstract

The 1, 3-dipolar cycloaddition of sugar ketonitrones is a useful synthetic procedure to build up nitrogenated quaternary centers in terms of scope (substrate, dipolarophile, inter-and intramolecular versions), yield, and regio-and stereoselectivity. The hybrid ONIOM (B3LYP/6- 31G (d): AM1) theoretical method followed by single-point energy calculations at the B3LYP/6-31G (d) level adequately perform to model this cycloaddition for the relatively ...

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