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Type: Artigo
Title: Enantioselective heck arylation of acyclic alkenol aryl ethers: synthetic applications and DFT investigation of the stereoselectivity
Author: Polo, Ellen Christine
Wang, Marti Fernandez
Angnes, Ricardo Almir
Braga, Ataualpa A. C.
Duarte Correia, Carlos Roque
Abstract: Herein we report the enantioselective Heck-Matsuda arylation of acyclic E and Z-alkenyl aryl ethers. The reactions were carried out under mild conditions affording the enantioenriched benzyl ethers in a regioselective manner, moderate to good yields (up to 73%), and in good to excellent enantiomeric ratios (up to 97:3). The enantioselective Heck-Matsuda arylation has shown a broad scope (25 examples), and some key Heck-Matsuda adducts were further converted into more complex and valuable scaffolds including their synthetic application in the synthesis of (R)-Fluoxetine, (R)-Atomoxetine, and in the synthesis of an enantioenriched benzo[c]chromene. Finally, in silico mechanistic investigations into the reaction's enantioselectivity were performed using density functional theory
Subject: Heck-Matsuda, reação de
Country: Alemanha
Editor: John Wiley & Sons
Rights: Fechado
Identifier DOI: 10.1002/adsc.201901471
Date Issue: 2019
Appears in Collections:IQ - Artigos e Outros Documentos

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