Ruthenium-catalyzed silyl ether formation and enyne metathesis sequence: synthesis of siloxacycles from terminal alkenyl alcohols and alkynylsilanes.
Org Lett. 2004 Aug 05; 6(16):2773-6.OL

Abstract

Two consecutive ruthenium-catalyzed reactions have been achieved for the synthesis of siloxacycles from terminal alkenyl carbenols and alkynylsilanes. The metal-catalyzed dehydrogenative condensation between alcohols and silanes, generating molecular hydrogen as the only byproduct, allows for the subsequent enyne metathesis without isolating the intermediate silyl ethers. This system provides a streamlined synthesis of synthetically useful building blocks. [reaction: see text]

Authors+Show Affiliations

Miller RL

Department of Chemistry, University of Wisconsin-Madison, Madison, WI 53706, USA.

Maifeld SV

No affiliation info available

Lee D

No affiliation info available

MeSH

AlcoholsAlkenesAlkynesCatalysisEthersMolecular StructureRutheniumSilanesSiloxanes

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

15281766

Citation

Miller, Reagan L., et al. "Ruthenium-catalyzed Silyl Ether Formation and Enyne Metathesis Sequence: Synthesis of Siloxacycles From Terminal Alkenyl Alcohols and Alkynylsilanes." Organic Letters, vol. 6, no. 16, 2004, pp. 2773-6.

Miller RL, Maifeld SV, Lee D. Ruthenium-catalyzed silyl ether formation and enyne metathesis sequence: synthesis of siloxacycles from terminal alkenyl alcohols and alkynylsilanes. Org Lett. 2004;6(16):2773-6.

Miller, R. L., Maifeld, S. V., & Lee, D. (2004). Ruthenium-catalyzed silyl ether formation and enyne metathesis sequence: synthesis of siloxacycles from terminal alkenyl alcohols and alkynylsilanes. Organic Letters, 6(16), 2773-6.

Miller RL, Maifeld SV, Lee D. Ruthenium-catalyzed Silyl Ether Formation and Enyne Metathesis Sequence: Synthesis of Siloxacycles From Terminal Alkenyl Alcohols and Alkynylsilanes. Org Lett. 2004 Aug 5;6(16):2773-6. PubMed PMID: 15281766.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Ruthenium-catalyzed silyl ether formation and enyne metathesis sequence: synthesis of siloxacycles from terminal alkenyl alcohols and alkynylsilanes. AU - Miller,Reagan L, AU - Maifeld,Sarah V, AU - Lee,Daesung, PY - 2004/7/30/pubmed PY - 2005/3/3/medline PY - 2004/7/30/entrez SP - 2773 EP - 6 JF - Organic letters JO - Org Lett VL - 6 IS - 16 N2 - Two consecutive ruthenium-catalyzed reactions have been achieved for the synthesis of siloxacycles from terminal alkenyl carbenols and alkynylsilanes. The metal-catalyzed dehydrogenative condensation between alcohols and silanes, generating molecular hydrogen as the only byproduct, allows for the subsequent enyne metathesis without isolating the intermediate silyl ethers. This system provides a streamlined synthesis of synthetically useful building blocks. [reaction: see text] SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/15281766/Ruthenium_catalyzed_silyl_ether_formation_and_enyne_metathesis_sequence:_synthesis_of_siloxacycles_from_terminal_alkenyl_alcohols_and_alkynylsilanes_ DB - PRIME DP - Unbound Medicine ER -

Tags

Ruthenium-catalyzed silyl ether formation and enyne metathesis sequence: synthesis of siloxacycles from terminal alkenyl alcohols and alkynylsilanes.Org Lett. 2004 Aug 05; 6(16):2773-6.OL