Ruthenium-Catalyzed Multicomponent Reactions: Access to α-Silyl-β-Hydroxy Vinylsilanes, Stereodefined 1,3-Dienes, and Cyclohexenes

Overview

Journal Chemistry

Specialty Chemistry

Date 2015 Dec 17

PMID 26669265

Citations 1

Authors

Barry M Trost

Dennis C Koester

Ehesan U Sharif

Affiliations

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Abstract

The synthesis of densly functionized α-silyl-β-hydroxyl vinylsilanes via ruthenium-catalyzed multicomponent reaction (MCR) is reported herein. Exceptionally high regio- and diastereoselectivity was achieved by employing an unprecedented hydrosilylation of bifunctional silyl-propargyl boronates. The simple protocol, mild reaction conditions, and unique tolerability of this method make it a valuable tool for the synthesis of highly elaborated building blocks. The one-pot synthesis of stereodefined olefins, the generation of a valuable cyclohexene building block through a four-component MCR, and further functionalization in an abundance of diastereoselective reactions is disclosed herein.

Citing Articles

Ru-catalyzed sequence for the synthesis of cyclic amido-ethers.

Trost B, Sharif E, Cregg J Chem Sci. 2017; 8(1):770-774.

PMID: 28451225 PMC: 5299796. DOI: 10.1039/c6sc02849g.

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