Regio- and Stereoselective Aminopentadienylation of Carbonyl Compounds

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Title: Regio- and Stereoselective Aminopentadienylation of Carbonyl Compounds
Authors: Bosque, Irene | Bagdatli, Emine | Foubelo, Francisco | Gonzalez-Gomez, Jose C.
Research Group/s: Catálisis Estereoselectiva en Síntesis Orgánica (CESO) | Síntesis Asimétrica (SINTAS)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Carbonyl compounds | Aminopentadienylation
Knowledge Area: Química Orgánica
Issue Date: 3-Feb-2014
Publisher: American Chemical Society
Citation: Journal of Organic Chemistry. 2014, 79(4): 1796-1804. doi:10.1021/jo402854z
Abstract: A simple and robust protocol is detailed for the preparation of enantioenriched α-substituted (1,4-pentadien-3-yl)amine derivatives. The methodology involves the addition of an in situ formed pentadienyl indium reagent to chiral tert-butylsulfinimines, previously formed in the same pot. The addition takes place with excellent γ-regio- and diastereoselectivity for a wide range of carbonyl compounds, including α-unsubstituted aldehydes and methyl alkyl ketones. The catalytic hydrogenation of the sulfinamines obtained provides a convenient access to chiral α-substituted (3-pentyl)amines. The hydroboration–oxidation of the α-(1,4-pentadien-3-yl)amine derivatives, followed by a cyclization under Mitsunobu conditions, takes place with an excellent diastereoselectivity governed by the chiral sulfinyl group.
Sponsor: We thank the Spanish Ministerio de Ciencia e Innovación (CTQ2011-24165) for financial support. I.B. acknowledges the Generalitat Valenciana for a predoctoral fellowship (ACIF/2011/159). E.B. acknowledges the Council of Higher Education- Turkey for a postdoctoral fellowship (16.10.12-B.09.6.YÖK.0.71.01-207.02-12285).
URI: http://hdl.handle.net/10045/37266
ISSN: 0022-3263 (Print) | 1520-6904 (Online)
DOI: 10.1021/jo402854z
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2014 American Chemical Society
Peer Review: si
Publisher version: http://dx.doi.org/10.1021/jo402854z
Appears in Collections:INV - CESO - Artículos de Revistas
INV - SINTAS - Artículos de Revistas

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