Diastereoselective Access to Polyoxygenated Polycyclic Spirolactones through a Rhodium??Catalyzed [3+ 2] Cycloaddition Reaction: Experimental and Theoretical …

…, JL Parrain, G Chouraqui, L Commeiras

Index: Rodier, Fabien; Rajzmann, Michel; Parrain, Jean-Luc; Chouraqui, Gaelle; Commeiras, Laurent Chemistry - A European Journal, 2013 , vol. 19, # 7 p. 2467 - 2477

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Citation Number: 10

Abstract

Abstract The synthetic utility of γ-alkylidenebutenolides is demonstrated as highly competent dipolarophile partners in both intra-and intermolecular rhodium (II)-catalyzed 1, 3-dipolar cycloaddition reactions. The strength of this approach lies in the formation of spiro [6, 4] lactone moieties with the concomitant construction of quaternary spiro stereocenters. Typically, the construction of spirolactones involves an esterification step, which has often ...