Tags

Type your tag names separated by a space and hit enter

Synthesis of alpha,beta-unsaturated 4,5-disubstituted gamma-lactones via ring-closing metathesis catalyzed by the first-generation Grubbs' catalyst.
Org Lett. 2005 Apr 28; 7(9):1805-8.OL

Abstract

[reaction: see text] 4-Methyl-5-alkyl-2(5H)-furanones have been prepared by ruthenium-catalyzed ring-closing metathesis of the suitable methallyl acrylates. Despite the electron deficiency of the conjugated double bond and of the gem-disubstitution of the allylic alkene moiety in the starting acrylates, the first-generation Grubbs' catalyst I proved to be an effective promoter for the ring closure, affording the expected butenolides in good to high yields.

Authors+Show Affiliations

Bassetti M
Istituto CNR di Metodologie Chimiche, Sezione Meccanismi di Reazione, Dipartimento di Chimica, Università degli Studi "La Sapienza", P.le Aldo Moro 5, 00185 Roma, Italy. mauro.bassetti@uniroma1.it
D'Annibale A
No affiliation info available
Fanfoni A
No affiliation info available
Minissi F
No affiliation info available

MeSH

AlkenesCatalysisCyclizationLactonesMolecular StructureRutheniumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

15844911

Citation

Bassetti, Mauro, et al. "Synthesis of Alpha,beta-unsaturated 4,5-disubstituted Gamma-lactones Via Ring-closing Metathesis Catalyzed By the First-generation Grubbs' Catalyst." Organic Letters, vol. 7, no. 9, 2005, pp. 1805-8.
Bassetti M, D'Annibale A, Fanfoni A, et al. Synthesis of alpha,beta-unsaturated 4,5-disubstituted gamma-lactones via ring-closing metathesis catalyzed by the first-generation Grubbs' catalyst. Org Lett. 2005;7(9):1805-8.
Bassetti, M., D'Annibale, A., Fanfoni, A., & Minissi, F. (2005). Synthesis of alpha,beta-unsaturated 4,5-disubstituted gamma-lactones via ring-closing metathesis catalyzed by the first-generation Grubbs' catalyst. Organic Letters, 7(9), 1805-8.
Bassetti M, et al. Synthesis of Alpha,beta-unsaturated 4,5-disubstituted Gamma-lactones Via Ring-closing Metathesis Catalyzed By the First-generation Grubbs' Catalyst. Org Lett. 2005 Apr 28;7(9):1805-8. PubMed PMID: 15844911.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Synthesis of alpha,beta-unsaturated 4,5-disubstituted gamma-lactones via ring-closing metathesis catalyzed by the first-generation Grubbs' catalyst. AU - Bassetti,Mauro, AU - D'Annibale,Andrea, AU - Fanfoni,Alessia, AU - Minissi,Franco, PY - 2005/4/23/pubmed PY - 2006/2/10/medline PY - 2005/4/23/entrez SP - 1805 EP - 8 JF - Organic letters JO - Org Lett VL - 7 IS - 9 N2 - [reaction: see text] 4-Methyl-5-alkyl-2(5H)-furanones have been prepared by ruthenium-catalyzed ring-closing metathesis of the suitable methallyl acrylates. Despite the electron deficiency of the conjugated double bond and of the gem-disubstitution of the allylic alkene moiety in the starting acrylates, the first-generation Grubbs' catalyst I proved to be an effective promoter for the ring closure, affording the expected butenolides in good to high yields. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/15844911/Synthesis_of_alphabeta_unsaturated_45_disubstituted_gamma_lactones_via_ring_closing_metathesis_catalyzed_by_the_first_generation_Grubbs'_catalyst_ DB - PRIME DP - Unbound Medicine ER -