Chiral Aminated α-Methylenebenzocycloalkenes from o-Bromoaryl Aldehydes and Ketones

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Title: Chiral Aminated α-Methylenebenzocycloalkenes from o-Bromoaryl Aldehydes and Ketones
Authors: Sirvent Pérez, Juan Alberto | Foubelo, Francisco | Yus, Miguel
Research Group/s: Síntesis Asimétrica (SINTAS)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Fused-ring systems | Allylation | Cyclization | Diastereoselectivity | Chiral auxiliaries | Indium
Knowledge Area: Química Orgánica
Issue Date: Apr-2013
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA
Citation: European Journal of Organic Chemistry. 2013, 2013(12): 2461-2471. doi:10.1002/ejoc.201201712
Abstract: Chiral tert-butylsulfinyl imines 3, which are easily prepared from the corresponding bromo carbonyl compounds 1 and tert-butanesulfinamide (2), undergo a diastereoselective allylation by using indium metal and allyl bromide to give the corresponding homoallyl sulfinylamines 4. Treatment of compounds 4 with a catalytic amount of palladium acetate and triphenylphosphane gives exo-methylene-substitutedsulfinylamino)benzocycloalkenes 5 (five- to seven-membered rings) that are easily deprotected with hydrochloric acid to give chiral primary amines 6.
Sponsor: The authors thank the Spanish Ministerio de Ciencia e Innovación (MICINN) (grant number CTQ2007-65218), the Consolider Ingenio (grant numbers 2010-CSD-2007-00006 and CTQ2011-24165), the Generalitat Valenciana (grant number PROMETEO/2009/039), the Fondos Europeos para el Desarrollo Regional (FEDER), and the University of Alicante for the financial support.
ISSN: 1434-193X (Print) | 1099-0690 (Online)
DOI: 10.1002/ejoc.201201712
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Peer Review: si
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Appears in Collections:INV - SINTAS - Artículos de Revistas

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