First asymmetric synthesis of a differentially silyl-protected tris(alkynyl)methyl methyl ether

First asymmetric synthesis of a differentially silyl-protected tris(alkynyl)methyl methyl ether

For an improved synthesis of the recently described expanded octamethoxycubane with a central C56 core, formally obtained by inserting buta-1,3-diynediyl moieties into all C(sp3)-C(sp3) bonds of octamethoxycubane, the preparation of the optically pure methyl ether of a differentially silyl-protected...

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Veröffentlicht in:Organic & biomolecular chemistry 2006-01, Vol.4 (7), p.1206-1208
Hauptverfasser: Convertino, Vito, Manini, Peter, Schweizer, W Bernd, Diederich, François
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container_title Organic & biomolecular chemistry
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creator Convertino, Vito
Manini, Peter
Schweizer, W Bernd
Diederich, François
description For an improved synthesis of the recently described expanded octamethoxycubane with a central C56 core, formally obtained by inserting buta-1,3-diynediyl moieties into all C(sp3)-C(sp3) bonds of octamethoxycubane, the preparation of the optically pure methyl ether of a differentially silyl-protected trispropargylic alcohol was required. The key step of the preparation involved a diastereoselective addition of a lithium acetylide to an optically active alkynyl ketone under Cram chelation control.
doi_str_mv 10.1039/b601380e
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source Royal Society of Chemistry Journals Archive (1841-2007); Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
title First asymmetric synthesis of a differentially silyl-protected tris(alkynyl)methyl methyl ether
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