Copper-Catalyzed Asymmetric Alkylation of β-Keto Esters with Xanthydrols

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Title: Copper-Catalyzed Asymmetric Alkylation of β-Keto Esters with Xanthydrols
Authors: Trillo Alarcón, María Paz | Baeza, Alejandro | Nájera, Carmen
Research Group/s: Síntesis Asimétrica (SINTAS) | Nuevos Materiales y Catalizadores (MATCAT)
Center, Department or Service: Universidad de Alicante. Departamento de Química Orgánica | Universidad de Alicante. Instituto Universitario de Síntesis Orgánica
Keywords: Alcohols | Asymmetric alkylation | Bisoxazolines | Copper | β-keto esters
Knowledge Area: Química Orgánica
Issue Date: 11-Oct-2013
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA
Citation: Advanced Synthesis & Catalysis. 2013, 355(14-15): 2815-2821. doi:10.1002/adsc.201300627
Abstract: The copper(II) triflate-tert-butyl-bisoxazoline [Cu(OTf)2-t-Bu-BOX]-catalyzed asymmetric alkylation of β-keto esters using free benzylic alcohols such as xanthydrols, as alkylating agents, is herein described for the first time. This green protocol renders in general the corresponding products with good results in terms of both yields and enantioselectivities using different keto esters, even when quaternary stereocenters were created. The scope, limitations and mechanistic aspects of the process are also discussed.
Sponsor: Spanish Ministerio de Ciencia e Innovación (MICINN) (projects CTQ2010-20387 and Consolider Ingenio 2010, CSD2007-00006), FEDER, the Generalitat Valenciana (PROMETEO 2009/039) and the University of Alicante are gratefully acknowledged for financial support. A. B. would also like to thank MICINN for a Juan de la Cierva contract (JCI-2009-03710) and the University of Alicante (Project GRE12-03).
URI: http://hdl.handle.net/10045/40228
ISSN: 1615-4150 (Print) | 1615-4169 (Online)
DOI: 10.1002/adsc.201300627
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Peer Review: si
Publisher version: http://dx.doi.org/10.1002/adsc.201300627
Appears in Collections:INV - MATCAT - Artículos de Revistas
INV - SINTAS - Artículos de Revistas
INV - AMIC - Artículos de Revistas

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