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Synthesis of Chiral 1,3-Dienes through Ring-Closing Metathesis of Enantioenriched Enynes: Potential Precursors of Morphane Analogs

Overview of attention for article published in Anais da Academia Brasileira de Ciências, January 2018
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Title
Synthesis of Chiral 1,3-Dienes through Ring-Closing Metathesis of Enantioenriched Enynes: Potential Precursors of Morphane Analogs
Published in
Anais da Academia Brasileira de Ciências, January 2018
DOI 10.1590/0001-3765201720170756
Pubmed ID
Authors

MARÍA JESÚS GARCIA-MUÑOZ, ANA SIRVENT, FRANCISCO FOUBELO, MIGUEL YUS

Abstract

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.

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Chemistry 1 100%