Abnormal Behaviour of Allenylsulfones under Lu's Reaction Conditions: Synthesis of Enantiopure Polyfunctionalised Cyclopentenes

…, MR Martín, A Fraile, JL García Ruano

Index: Nunez Jr., Alberto; Rosario Martin; Fraile, Alberto; Garcia Ruano, Jose L. Chemistry - A European Journal, 2010 , vol. 16, # 18 p. 5443 - 5453

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Citation Number: 21

Abstract

Abstract Formal [3+ 2] cycloadditions of 5-alkoxyfuran-2 (5H)-ones 1 and 2 with allenylsulfones 3–5, promoted by different nucleophiles, afford 3-alkoxy-5-arylsulfonyl-3, 3 a, 6, 6 a-tetrahydro-1H-cyclopenta [c] furan-1-ones in good yields with complete control of both regio-and π-facial selectivity. The incorporation of a sulfinyl group on the furanone ring enhances the reactivity of the furanones and allows the synthesis of optically pure, bicyclic ...

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