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A Ru-catalyzed tandem alkyne-enone coupling/Michael addition: synthesis of 4-methylene-2,6-cis-tetrahydropyrans.
Org Lett. 2005 Oct 13; 7(21):4761-4.OL

Abstract

[reaction: see text] A Ru-catalyzed tandem alkyne-enone coupling/Michael addition reaction is reported. It provides an efficient, atom-economic entry to 4-methylene-2,6-cis-tetrahydropyrans from simple, readily available homopropargylic alcohols and beta,gamma-unsaturated enones in good yields. Further functionalization of the resultant vinylsilane leads to the synthesis of either geometrically defined trisubstituted alkene exocyclic to the 2,6-cis-dihydropyran.

Authors+Show Affiliations

Trost BM
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
Yang H
No affiliation info available
Wuitschik G
No affiliation info available

MeSH

AlkenesAlkynesCatalysisKetonesMolecular StructurePyransRuthenium

Pub Type(s)

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

Language

eng

PubMed ID

16209529

Citation

Trost, Barry M., et al. "A Ru-catalyzed Tandem Alkyne-enone coupling/Michael Addition: Synthesis of 4-methylene-2,6-cis-tetrahydropyrans." Organic Letters, vol. 7, no. 21, 2005, pp. 4761-4.
Trost BM, Yang H, Wuitschik G. A Ru-catalyzed tandem alkyne-enone coupling/Michael addition: synthesis of 4-methylene-2,6-cis-tetrahydropyrans. Org Lett. 2005;7(21):4761-4.
Trost, B. M., Yang, H., & Wuitschik, G. (2005). A Ru-catalyzed tandem alkyne-enone coupling/Michael addition: synthesis of 4-methylene-2,6-cis-tetrahydropyrans. Organic Letters, 7(21), 4761-4.
Trost BM, Yang H, Wuitschik G. A Ru-catalyzed Tandem Alkyne-enone coupling/Michael Addition: Synthesis of 4-methylene-2,6-cis-tetrahydropyrans. Org Lett. 2005 Oct 13;7(21):4761-4. PubMed PMID: 16209529.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A Ru-catalyzed tandem alkyne-enone coupling/Michael addition: synthesis of 4-methylene-2,6-cis-tetrahydropyrans. AU - Trost,Barry M, AU - Yang,Hanbiao, AU - Wuitschik,Georg, PY - 2005/10/8/pubmed PY - 2006/8/9/medline PY - 2005/10/8/entrez SP - 4761 EP - 4 JF - Organic letters JO - Org Lett VL - 7 IS - 21 N2 - [reaction: see text] A Ru-catalyzed tandem alkyne-enone coupling/Michael addition reaction is reported. It provides an efficient, atom-economic entry to 4-methylene-2,6-cis-tetrahydropyrans from simple, readily available homopropargylic alcohols and beta,gamma-unsaturated enones in good yields. Further functionalization of the resultant vinylsilane leads to the synthesis of either geometrically defined trisubstituted alkene exocyclic to the 2,6-cis-dihydropyran. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/16209529/A_Ru_catalyzed_tandem_alkyne_enone_coupling/Michael_addition:_synthesis_of_4_methylene_26_cis_tetrahydropyrans_ DB - PRIME DP - Unbound Medicine ER -