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Efficient synthesis of alkynylsilyl ethers and silaketals via base-induced alkynylsilane alcoholysis.
J Org Chem. 2004 Dec 10; 69(25):8967-70.JO

Abstract

The efficient silylation of alcohols with di- and trialkynylsilanes was achieved under base-catalyzed conditions to afford alkynyl silyl ethers and symmetrical alkynyl silaketals in good yield. A selective alcoholysis of dialkynyl silyl ethers to mixed silaketals was also demonstrated. These products served as substrates for enyne ring-closing metathesis and, consequently, as precursors to stereochemically defined 1,3-dienes.

Authors+Show Affiliations

Grimm JB
Department of Chemistry, University of Wisconsin-Madison, Madison, WI 53706, USA.
Lee D
No affiliation info available

MeSH

AlcoholsAlkaliesCatalysisEthersMolecular StructureOrganometallic CompoundsSilanes

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

15575786

Citation

Grimm, Jonathan B., and Daesung Lee. "Efficient Synthesis of Alkynylsilyl Ethers and Silaketals Via Base-induced Alkynylsilane Alcoholysis." The Journal of Organic Chemistry, vol. 69, no. 25, 2004, pp. 8967-70.
Grimm JB, Lee D. Efficient synthesis of alkynylsilyl ethers and silaketals via base-induced alkynylsilane alcoholysis. J Org Chem. 2004;69(25):8967-70.
Grimm, J. B., & Lee, D. (2004). Efficient synthesis of alkynylsilyl ethers and silaketals via base-induced alkynylsilane alcoholysis. The Journal of Organic Chemistry, 69(25), 8967-70.
Grimm JB, Lee D. Efficient Synthesis of Alkynylsilyl Ethers and Silaketals Via Base-induced Alkynylsilane Alcoholysis. J Org Chem. 2004 Dec 10;69(25):8967-70. PubMed PMID: 15575786.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Efficient synthesis of alkynylsilyl ethers and silaketals via base-induced alkynylsilane alcoholysis. AU - Grimm,Jonathan B, AU - Lee,Daesung, PY - 2004/12/4/pubmed PY - 2005/2/16/medline PY - 2004/12/4/entrez SP - 8967 EP - 70 JF - The Journal of organic chemistry JO - J Org Chem VL - 69 IS - 25 N2 - The efficient silylation of alcohols with di- and trialkynylsilanes was achieved under base-catalyzed conditions to afford alkynyl silyl ethers and symmetrical alkynyl silaketals in good yield. A selective alcoholysis of dialkynyl silyl ethers to mixed silaketals was also demonstrated. These products served as substrates for enyne ring-closing metathesis and, consequently, as precursors to stereochemically defined 1,3-dienes. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/15575786/Efficient_synthesis_of_alkynylsilyl_ethers_and_silaketals_via_base_induced_alkynylsilane_alcoholysis_ DB - PRIME DP - Unbound Medicine ER -