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Anais da Academia Brasileira de Ciências

Print version ISSN 0001-3765On-line version ISSN 1678-2690

Abstract

GARCIA-MUNOZ, MARÍA JESÚS; SIRVENT, ANA; FOUBELO, FRANCISCO  and  YUS, MIGUEL. Synthesis of Chiral 1,3-Dienes through Ring-Closing Metathesis of Enantioenriched Enynes: Potential Precursors of Morphane Analogs. An. Acad. Bras. Ciênc. [online]. 2018, vol.90, n.1, suppl.2, pp.1059-1072. ISSN 0001-3765.  http://dx.doi.org/10.1590/0001-3765201720170756.

A simple methodology for the synthesis of enynes by indium mediated diastereoselective allylation of aromatic N-tert-butanesulfinylimines bearing alkenyl groups at ortho-position with allyl bromide has been developed. The addition of the allyl indium intermediate to the chiral imine took place with excellent diastereoselectivity. Ruthenium-catalyzed ring-closing metathesis of the resulting enynes provided the expected cyclic 1,3-dienes in good to moderate yields. These chiral dienes are potential precursors of biologically and pharmacologically active morphane derivatives.

Keywords : allylation; imines; dienes; enynes; metathesis; alkaloids.

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