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Issue 2, 2016
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Rhodium-catalyzed asymmetric synthesis of silicon-stereogenic silicon-bridged arylpyridinones

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Abstract

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.

Graphical abstract: Rhodium-catalyzed asymmetric synthesis of silicon-stereogenic silicon-bridged arylpyridinones

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Supplementary files

Article information


Submitted
05 Oct 2015
Accepted
06 Nov 2015
First published
09 Nov 2015

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2016,7, 1205-1211
Article type
Edge Article
Author version available

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

R. Shintani, R. Takano and K. Nozaki, Chem. Sci., 2016, 7, 1205
DOI: 10.1039/C5SC03767K

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