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Diastereoselective Homoallylation and bis-homoallylation of N-tertbutanesulfinyl Imines with Organomagnesium Compounds

[ Vol. 15 , Issue. 5 ]

Author(s):

Ana Sirvent and Francisco Foubelo*   Pages 345 - 348 ( 4 )

Abstract:


The addition of but-3-enylmagnesium bromide and pent-4-enylmagnesium bromide to N-tert-butanesulfinyl aldimines in toluene as solvent proceeds with high diastereoselectivity to yield the corresponding products of homoallylation and bis-homoallylation, respectively. The reactions are diastereoselective, and the configuration of the sulfur atom of the sulfinyl group determined the stereochemical outcome. The reaction products are aminoalkene derivatives of potential synthetic interest as precursors of nitrogen containing heterocycles.

Keywords:

Homoallylation, bis-homoallylation, diastereoselective addition, N-tert-butanesulfinyl imines, grignard reagents, heterocycles.

Affiliation:

Departamento de Quimica Organica, Instituto de Sintesis Organica, and Centro de Innovacion en Quimica Avanzada (ORFEO-CINQA), Universidad de Alicante, Apdo. 99, 03080 Alicante, Departamento de Quimica Organica, Instituto de Sintesis Organica, and Centro de Innovacion en Quimica Avanzada (ORFEO-CINQA), Universidad de Alicante, Apdo. 99, 03080 Alicante

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