New transient arenesulfenic acids were involved in the synthesis of enantiopure 2-arylsulfinyl-1,3-dienes, showing central or axial chirality of the substituted arene residue, apart from the chirality related to the stereogenic sulfur atom. Some of the obtained dienes, that is, (Sa,SS)- and (SaRS)-2-(20-hydroxy-1,10-binaphthalen-2-sulfinyl)-3-methyl-1,3-butadienes, were subjected to diastereoselective Diels– Alder cycloadditions with N-methylmaleimide. Removal of the arylsulfoxide auxiliary, in the major adduct, was accomplished by reductive cleavage with Raney nickel

Enantiopure arenesulfenic acids as intermediates in stereoselective synthesis / M. C. Aversa; P. Bonaccorsi; C. Faggi; G. Lamanna; S. Menichetti. - In: TETRAHEDRON. - ISSN 0040-4020. - STAMPA. - 61:(2005), pp. 11902-11909.

Enantiopure arenesulfenic acids as intermediates in stereoselective synthesis

FAGGI, CRISTINA;MENICHETTI, STEFANO
2005

Abstract

New transient arenesulfenic acids were involved in the synthesis of enantiopure 2-arylsulfinyl-1,3-dienes, showing central or axial chirality of the substituted arene residue, apart from the chirality related to the stereogenic sulfur atom. Some of the obtained dienes, that is, (Sa,SS)- and (SaRS)-2-(20-hydroxy-1,10-binaphthalen-2-sulfinyl)-3-methyl-1,3-butadienes, were subjected to diastereoselective Diels– Alder cycloadditions with N-methylmaleimide. Removal of the arylsulfoxide auxiliary, in the major adduct, was accomplished by reductive cleavage with Raney nickel
61
11902
11909
M. C. Aversa; P. Bonaccorsi; C. Faggi; G. Lamanna; S. Menichetti
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/2158/253918
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