Issue 2, 2016

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

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

Supplementary files

Article information

Article type
Edge Article
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
Creative Commons BY-NC license

Chem. Sci., 2016,7, 1205-1211

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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