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Regioselective Nucleophilic Addition to Carbonyl Ylide Intermediates:  A Novel Diastereoselective Synthesis of Cycloalkyl Fused Furan-3-ones

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journal contribution
posted on 13.10.2005, 00:00 by Sengodagounder Muthusamy, Boopathy Gnanaprakasam, Eringathodi Suresh
A range of cis-fused hexahydro-1-benzofuran-3(2H)-one or tetrahydro-2H-cyclopenta[b]furan-3(3aH)-one ring systems was synthesized by the rhodium(II) acetate catalyzed reaction of α-diazo carbonyl compounds in the presence of various oxygen, nitrogen, and sulfur nucleophiles. A double-nucleophilic addition was possible by using an excess of α-diazo ketone. These reactions proceeded with complete diastereoselectivity, and the stereochemistry was confirmed by the single-crystal X-ray analysis. This process discloses the first example of tandem cyclization−nucleophilic addition reaction.