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

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

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Parrain, Jean-luc Chouraqui, Gaëlle Commeiras, Laurent Rodier, Fabien Rajzmann, Michel
Description	Author Affiliation: Rodier F ( Aix-Marseille Université, Institut des Sciences Moléculaires de Marseille iSm2, UMR AMU-CNRS 7313, service 532, Campus scientifique de Saint Jérôme, 13397 Marseille cedex 20, France.)
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 been reported as a “biosynthetic pathway”, and often occurs either as or near to the final step of a total synthesis. Furthermore, a convergent and versatile route is reported for the formation of the (5,7) skeleton of molecules that were isolated from the Schisandra genus. Computational studies were performed to provide an overall picture of the mechanism of the intermolecular [3+2] cycloaddition between 2-diazo-1,3-ketoester and protoanemonin and to rationalize the empirical observations. In particular, we have demonstrated for the first time that the rhodium center plays an important role during the cyclization step itself and reacts with the dipolarophile as a complex with the ylide.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	7
Volume Number	19
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2013-02-11
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Lactones Chemistry Polycyclic Compounds Rhodium Spiro Compounds Cycloaddition Reaction Ligands Models, Theoretical Molecular Structure Stereoisomerism Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

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