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

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.

journal_name

An Acad Bras Cienc

authors

Garcia-Muñoz MJ,Sirvent A,Foubelo F,Yus M

doi

10.1590/0001-3765201720170756

subject

Has Abstract

pub_date

2018-01-01 00:00:00

pages

1059-1072

issue

1 Suppl 2

eissn

0001-3765

issn

1678-2690

pii

S0001-37652018000301059

journal_volume

90

pub_type

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