Diastereoselective Coupling of 1,3-Diene, Ketone, and Organometallic Reagents by Nickel Catalyst

Diastereoselective Coupling of 1,3-Diene, Ketone, and Organometallic Reagents by Nickel Catalyst

A nickel-catalyzed three-component coupling of 1,3-diene, ketone, and organoboron or organosilicon reagents was investigated. While the coupling reaction using PhB(OH)2 afforded a 1,3-syn-substituted 4-penten-1-ol derivative as a single diastereomer, the reaction in the presence of tetraorganosilico...

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Veröffentlicht in:Chemistry letters 2009-06, Vol.38 (6), p.594
Hauptverfasser: Saito, Nozomi, Yamazaki, Tetsuro, Sato, Yoshihiro
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Yamazaki, Tetsuro
Sato, Yoshihiro
description A nickel-catalyzed three-component coupling of 1,3-diene, ketone, and organoboron or organosilicon reagents was investigated. While the coupling reaction using PhB(OH)2 afforded a 1,3-syn-substituted 4-penten-1-ol derivative as a single diastereomer, the reaction in the presence of tetraorganosilicon reagent under similar conditions exclusively produced the corresponding 1,3-anti isomer. In both reactions, a tetrasubstituted carbon center was constructed in a highly diastereoselective manner.
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source Oxford University Press Journals All Titles (1996-Current)
title Diastereoselective Coupling of 1,3-Diene, Ketone, and Organometallic Reagents by Nickel Catalyst
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