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Abnormal Behaviour of Allenylsulfones under Lu’s Reaction Conditions: Synthesis of Enantiopure Polyfunctionalised Cyclopentenes
Author(s) -
Núñez Alberto,
Martín M. Rosario,
Fraile Alberto,
García Ruano José L.
Publication year - 2010
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200903185
Subject(s) - enantiopure drug , bicyclic molecule , nucleophile , chemistry , furan , selectivity , adduct , ring (chemistry) , cyclopentanes , reactivity (psychology) , stereochemistry , medicinal chemistry , organic chemistry , enantioselective synthesis , catalysis , medicine , alternative medicine , pathology
Abstract Formal [3+2] cycloadditions of 5‐alkoxyfuran‐2(5 H )‐ones 1 and 2 with allenylsulfones 3 – 5 , promoted by different nucleophiles, afford 3‐alkoxy‐5‐arylsulfonyl‐3,3 a,6,6 a‐tetrahydro‐1 H ‐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 adducts in good yields. Allenylsulfones evolve through a different mechanism to that proposed for allenoates (Lu’s reaction) and afford bicyclic adducts in which the sulfonyl group is joined to C‐5. This has advantages on the stereochemical control of further reactions leading to enantiomerically pure polyfunctionalised cyclopentenes and cyclopentanes.