Journal
ANAIS DA ACADEMIA BRASILEIRA DE CIENCIAS
Volume 90, Issue -, Pages 1059-1072Publisher
ACAD BRASILEIRA DE CIENCIAS
DOI: 10.1590/0001-3765201720170756
Keywords
allylation; imines; dienes; enynes; metathesis; alkaloids
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Funding
- Ministerio de Ciencia e Innovacion (MCINN) [CONSOLIDER INGENIO 2010-CDS2007-00006, CTQ2011-24165]
- Ministerio de Economia y Competitividad (MINECO) [CTQ2014-53695-P, CTQ2014-51912-REDC, CTQ2016-81797-REDC, CTQ2017-85093-P]
- FEDER
- Generalitat Valenciana [PROMETEO 2009/039, PROMETEOII/2014/017]
- University of Alicante
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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 diastercoselectivity. 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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