Enantioselective addition of alkynyl ketones to nitroolefins assisted by Brønsted base/H-bonding catalysis
Date
2019Author
Version
Acceso abierto / Sarbide irekia
Type
Artículo / Artikulua
Version
Versión aceptada / Onetsi den bertsioa
Project Identifier
ES/1PE/CTQ2016-78487
Impact
|
10.1002/chem.201805542
Abstract
Various sets of enolizable alkynyl ketones (including methyl ynones with α-aryl, α-alkenyl, and α-alkoxy groups) were able to react smoothly with nitroolefins with the assistance of bifunctional Brønsted base/H-bond catalysts to provide adducts with two consecutive tertiary stereocenters in a highly diastereo- and enantioselective fashion. Further transformation of the obtained adducts into optic ...
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Various sets of enolizable alkynyl ketones (including methyl ynones with α-aryl, α-alkenyl, and α-alkoxy groups) were able to react smoothly with nitroolefins with the assistance of bifunctional Brønsted base/H-bond catalysts to provide adducts with two consecutive tertiary stereocenters in a highly diastereo- and enantioselective fashion. Further transformation of the obtained adducts into optically active acyclic and polycyclic molecules, including some with intricate carbon skeletons, was also demonstrated. [--]
Subject
Alkynyl ketones,
Asymmetric catalysis,
Brønsted bases,
Michael reaction,
Organocatalysis
Publisher
Wiley
Published in
Chemistry: A European Journal, 2019, 25 (17), 4390-4397
Departament
Universidad Pública de Navarra. Departamento de Ciencias /
Nafarroako Unibertsitate Publikoa. Zientziak Saila /
Universidad Pública de Navarra / Nafarroako Unibertsitate Publikoa. INAMAT2 - Institute for Advanced Materials and Mathematics
Publisher version
Sponsorship
Financial support was provided by the University of the Basque Country UPV/EHU (UFI QOSYC 11/22), Basque Government (BG Grant No IT-628-13), and Ministerio de Economía y Competitividad (MINECO, Grant CTQ2016-78487-C2), Spain, T.C. thanks MINECO, and I.I. and O.O. thank BG for fellowships.