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Regio- and stereoselective synthesis of 2-amino-1,3-diene derivatives by ruthenium-catalyzed coupling of ynamides and ethylene.
Org Lett. 2011 May 20; 13(10):2718-21.OL

Abstract

A ruthenium-catalyzed hydrovinylation-type cross-coupling of ynamides and ethylene proceeds via ruthenacyclopentene to give 2-aminobuta-1,3-diene derivatives in a highly regioselective manner. It was also demonstrated that 2-aminobuta-1,3-diene derivatives reacted with various dienophiles or singlet oxygen to give a cyclic enamide derivative.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Saito N
Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan. nozomi-s@pharm.hokudai.ac.jp
Saito K
No affiliation info available
Shiro M
No affiliation info available
Sato Y
No affiliation info available

MeSH

AlkadienesAlkynesAmidesCatalysisEthylenesMolecular StructureRutheniumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

21510622

Citation

Saito, Nozomi, et al. "Regio- and Stereoselective Synthesis of 2-amino-1,3-diene Derivatives By Ruthenium-catalyzed Coupling of Ynamides and Ethylene." Organic Letters, vol. 13, no. 10, 2011, pp. 2718-21.
Saito N, Saito K, Shiro M, et al. Regio- and stereoselective synthesis of 2-amino-1,3-diene derivatives by ruthenium-catalyzed coupling of ynamides and ethylene. Org Lett. 2011;13(10):2718-21.
Saito, N., Saito, K., Shiro, M., & Sato, Y. (2011). Regio- and stereoselective synthesis of 2-amino-1,3-diene derivatives by ruthenium-catalyzed coupling of ynamides and ethylene. Organic Letters, 13(10), 2718-21. https://doi.org/10.1021/ol200812y
Saito N, et al. Regio- and Stereoselective Synthesis of 2-amino-1,3-diene Derivatives By Ruthenium-catalyzed Coupling of Ynamides and Ethylene. Org Lett. 2011 May 20;13(10):2718-21. PubMed PMID: 21510622.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Regio- and stereoselective synthesis of 2-amino-1,3-diene derivatives by ruthenium-catalyzed coupling of ynamides and ethylene. AU - Saito,Nozomi, AU - Saito,Keiichi, AU - Shiro,Motoo, AU - Sato,Yoshihiro, Y1 - 2011/04/21/ PY - 2011/4/23/entrez PY - 2011/4/23/pubmed PY - 2011/7/27/medline SP - 2718 EP - 21 JF - Organic letters JO - Org Lett VL - 13 IS - 10 N2 - A ruthenium-catalyzed hydrovinylation-type cross-coupling of ynamides and ethylene proceeds via ruthenacyclopentene to give 2-aminobuta-1,3-diene derivatives in a highly regioselective manner. It was also demonstrated that 2-aminobuta-1,3-diene derivatives reacted with various dienophiles or singlet oxygen to give a cyclic enamide derivative. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/21510622/Regio__and_stereoselective_synthesis_of_2_amino_13_diene_derivatives_by_ruthenium_catalyzed_coupling_of_ynamides_and_ethylene_ L2 - https://doi.org/10.1021/ol200812y DB - PRIME DP - Unbound Medicine ER -