Copper-Catalyzed Asymmetric Allylic Alkylation of β-Keto Esters with Allylic Alcohols

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Title: Copper-Catalyzed Asymmetric Allylic Alkylation of β-Keto Esters with Allylic Alcohols
Authors: Trillo Alarcón, María Paz | Baeza, Alejandro
Research Group/s: 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: Asymmetric Allylic Alkylation | Allylic Alcohols | β-Keto esters | Copper | Bisoxazolines
Knowledge Area: Química Orgánica
Issue Date: 17-May-2017
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA
Citation: Advanced Synthesis & Catalysis. 2017, 359(10): 1735-1741. doi:10.1002/adsc.201601139
Abstract: The asymmetric allylic alkylation reaction of β-keto esters catalyzed by copper complex tBuBOX-Cu(OTf)2 employing allylic alcohols as environmentally friendly electrophilic partner, is herein described. This new protocol renders in general the corresponding allylic products with two consecutive all-carbon stereocenters in good both yields and enantioselectivities and with low to modest diastereoselection. The regioselectivity of the process seems to be governed by the formation of the most stable olefin according to the results obtained when non-symmetrically substituted alcohols were employed. The scope, limitations and mechanistic aspects of the process are also discussed.
Sponsor: University of Alicante (VIGROB-173, GRE12-03), and Spanish Ministerio de Economía y Competitividad (CTQ2015-66624-P) are gratefully acknowledged for financial support (Project).
URI: http://hdl.handle.net/10045/66508
ISSN: 1615-4150 (Print) | 1615-4169 (Online)
DOI: 10.1002/adsc.201601139
Language: eng
Type: info:eu-repo/semantics/article
Rights: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Peer Review: si
Publisher version: http://dx.doi.org/10.1002/adsc.201601139
Appears in Collections:INV - MATCAT - Artículos de Revistas
INV - AMIC - Artículos de Revistas

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