Journal ArticleDOI
Basic character of rare earth metal alkoxides. Utilization in catalytic C-C bond-forming reactions and catalytic asymmetric nitroaldol reactions
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In this article, the authors reported several carbon-carbon bond-forming reactions catalyzed by rare earth metal alkoxides and their application to a catalytic asymmetric nitroaldol reaction.Abstract:
In a recent paper, the authors reported that Zr(O-t-Bu){sub 4} was an efficient and convenient basic reagent in organic synthesis. However, all reactions examined were performed with stoichiometric quantities of the reagent. The authors envisioned that rare earth metal alkoxides would be stronger bases than group 4 metal alkoxides due to the lower ionization potential (ca. 5.4-6.4 eV) and the lower electronegativity (1.1-1.3) of rare earth elements; thus, the catalytic use of rare earth metal alkoxides in organic synthesis was expected. Although a variety of rare earth metal alkoxides have been prepared for the last three decades, to the authors knowledge, there have been few reports concerning the basicity of rare earth metal alkoxides. Herein, the authors report several carbon-carbon bond-forming reactions catalyzed by rare earth metal alkoxides and their application to a catalytic asymmetric nitroaldol reaction.read more
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Asymmetrische Katalyse mit Hetero‐Dimetall‐Verbindungen
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Tandem Catalytic Asymmetric Friedel–Crafts/Henry Reaction: Control of Three Contiguous Acyclic Stereocenters
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Heteromultimetallic catalysis for sustainable organic syntheses.
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Group 11 metal amide-catalyzed asymmetric cycloaddition reactions of azomethine imines with terminal alkynes.
TL;DR: A 1,3-dipolar cycloaddition reaction of azomethine imines with terminal alkynes catalyzed by group 11 metal amides to provide N,N-bicyclic pyrazolidinone derivatives was developed and the desired heterocycles were produced in high yields with exclusive regioselectivities and high enantioselectivity.
Journal ArticleDOI
Catalytic asymmetric nitroaldol reaction: An efficient synthesis of (S) propranolol using the lanthanum binaphthol complex
TL;DR: Propranolol, a more potent optical isomer of the widely used β-blocker, was conveniently synthesized in a higly enantioselective manner by the lanthanum-(R )-(+)-binaphthol complex catalyzed asymmetric nitroaldol reaction as discussed by the authors.
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