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Ruthenium-catalyzed cyclocarbonylation of allenyl alcohols and amines: selective synthesis of lactones and lactams.
J Org Chem. 2003 Oct 31; 68(22):8571-6.JO

Abstract

Allenyl alcohols such as 4-hydroxybuta-1,2-dienes and 5-hydroxypenta-1,2-dienes having a variety of substituents undergo cyclocarbonylation in the presence of a ruthenium catalyst under mild conditions selectively to give five- and six-membered lactones in a high yield with 100% atom economy. 5-Aminopenta-1,2-dines are also cyclocarbonylated to give gamma-lactams. A possible carbonylation mechanism involving a ruthenium cluster intermediate is proposed on the basis of experimental results.

Authors+Show Affiliations

Yoneda E
The Institute of Scientific and Industrial Research, Osaka University, Mihogaoka, Ibaraki, Osaka 567-0047, Japan.
Zhang SW
No affiliation info available
Zhou DY
No affiliation info available
Onitsuka K
No affiliation info available
Takahashi S
No affiliation info available

MeSH

AlcoholsAlkadienesAminesCatalysisCyclizationIsomerismLactamsLactonesModels, ChemicalOrganometallic CompoundsRuthenium

Pub Type(s)

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

Language

eng

PubMed ID

14575487

Citation

Yoneda, Eiji, et al. "Ruthenium-catalyzed Cyclocarbonylation of Allenyl Alcohols and Amines: Selective Synthesis of Lactones and Lactams." The Journal of Organic Chemistry, vol. 68, no. 22, 2003, pp. 8571-6.
Yoneda E, Zhang SW, Zhou DY, et al. Ruthenium-catalyzed cyclocarbonylation of allenyl alcohols and amines: selective synthesis of lactones and lactams. J Org Chem. 2003;68(22):8571-6.
Yoneda, E., Zhang, S. W., Zhou, D. Y., Onitsuka, K., & Takahashi, S. (2003). Ruthenium-catalyzed cyclocarbonylation of allenyl alcohols and amines: selective synthesis of lactones and lactams. The Journal of Organic Chemistry, 68(22), 8571-6.
Yoneda E, et al. Ruthenium-catalyzed Cyclocarbonylation of Allenyl Alcohols and Amines: Selective Synthesis of Lactones and Lactams. J Org Chem. 2003 Oct 31;68(22):8571-6. PubMed PMID: 14575487.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Ruthenium-catalyzed cyclocarbonylation of allenyl alcohols and amines: selective synthesis of lactones and lactams. AU - Yoneda,Eiji, AU - Zhang,Shi-Wei, AU - Zhou,Da-Yang, AU - Onitsuka,Kiyotaka, AU - Takahashi,Shigetoshi, PY - 2003/10/25/pubmed PY - 2004/3/18/medline PY - 2003/10/25/entrez SP - 8571 EP - 6 JF - The Journal of organic chemistry JO - J Org Chem VL - 68 IS - 22 N2 - Allenyl alcohols such as 4-hydroxybuta-1,2-dienes and 5-hydroxypenta-1,2-dienes having a variety of substituents undergo cyclocarbonylation in the presence of a ruthenium catalyst under mild conditions selectively to give five- and six-membered lactones in a high yield with 100% atom economy. 5-Aminopenta-1,2-dines are also cyclocarbonylated to give gamma-lactams. A possible carbonylation mechanism involving a ruthenium cluster intermediate is proposed on the basis of experimental results. SN - 0022-3263 UR - https://www.unboundmedicine.com/medline/citation/14575487/Ruthenium_catalyzed_cyclocarbonylation_of_allenyl_alcohols_and_amines:_selective_synthesis_of_lactones_and_lactams_ DB - PRIME DP - Unbound Medicine ER -