Rhodium-catalyzed asymmetric synthesis of silicon-stereogenic silicon-bridged arylpyridinones

A rhodium-catalyzed regio- and enantioselective synthesis of silicon-stereogenic silicon-bridged arylpyridinones has been developed through [2 + 2 + 2] cycloaddition of silicon-containing prochiral triynes with isocyanates. High yields and enantioselectivities have been achieved by employing an axia...

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Veröffentlicht in:	Chemical science (Cambridge) 2016-01, Vol.7 (2), p.125-1211
Hauptverfasser:	Shintani, Ryo, Takano, Ryo, Nozaki, Kyoko
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Sprache:	eng
Schlagworte:	Asymmetry Catalysis Catalysts Chemistry Cycloaddition Ligands Polymers Rhodium Synthesis
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creator	Shintani, Ryo Takano, Ryo Nozaki, Kyoko
description	A rhodium-catalyzed regio- and enantioselective synthesis of silicon-stereogenic silicon-bridged arylpyridinones has been developed through [2 + 2 + 2] cycloaddition of silicon-containing prochiral triynes with isocyanates. High yields and enantioselectivities have been achieved by employing an axially chiral monophosphine ligand, and this process could be applied to catalytic asymmetric synthesis of silicon-stereogenic chiral polymers for the first time. The reaction mechanism of the present catalysis has also been experimentally investigated to establish a reasonable catalytic cycle, advancing the mechanistic understanding of the rhodium-catalyzed pyridinone synthesis by [2 + 2 + 2] cycloaddition reactions. A rhodium-catalyzed regio- and enantioselective synthesis of silicon-stereogenic silicon-bridged arylpyridinones was developed. A reasonable catalytic cycle was also experimentally established.
doi_str_mv	10.1039/c5sc03767k
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subjects	Asymmetry Catalysis Catalysts Chemistry Cycloaddition Ligands Polymers Rhodium Synthesis
title	Rhodium-catalyzed asymmetric synthesis of silicon-stereogenic silicon-bridged arylpyridinones
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