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Palladium-catalyzed ring expansion reaction of (Z)-1-(1,3-butadienyl)cyclobutanols with aryl iodides. stereospecific synthesis of (Z)-2-(3-aryl-1-propenyl)cyclopentanones.
Org Lett. 2004 Jun 10; 6(12):1979-82.OL

Abstract

[reaction: see text] A novel type of cascade ring expansion process has been developed by the palladium-catalyzed reaction of (Z)-1-(1,3-butadienyl)cyclobutanols with aryl iodides. The reaction proceeds in a stereospecific manner to produce (Z)-2-(3-aryl-1-propenyl)cyclopentanones. It has also been found that regioselective alpha-arylation of alkenyl cyclopentanones proceeds to afford the alpha-arylated cyclopentanones.

Authors+Show Affiliations

Yoshida M
Department of Organic Chemistry, Graduate School of Pharmaceutical Sciences, Tohoku University, Aobayama, Sendai 980-8578, Japan.
Sugimoto K
No affiliation info available
Ihara M
No affiliation info available

MeSH

ButanolsCatalysisCyclizationCyclopentanesHydrocarbons, IodinatedMolecular ConformationPalladiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

15176798

Citation

Yoshida, Masahiro, et al. "Palladium-catalyzed Ring Expansion Reaction of (Z)-1-(1,3-butadienyl)cyclobutanols With Aryl Iodides. Stereospecific Synthesis of (Z)-2-(3-aryl-1-propenyl)cyclopentanones." Organic Letters, vol. 6, no. 12, 2004, pp. 1979-82.
Yoshida M, Sugimoto K, Ihara M. Palladium-catalyzed ring expansion reaction of (Z)-1-(1,3-butadienyl)cyclobutanols with aryl iodides. stereospecific synthesis of (Z)-2-(3-aryl-1-propenyl)cyclopentanones. Org Lett. 2004;6(12):1979-82.
Yoshida, M., Sugimoto, K., & Ihara, M. (2004). Palladium-catalyzed ring expansion reaction of (Z)-1-(1,3-butadienyl)cyclobutanols with aryl iodides. stereospecific synthesis of (Z)-2-(3-aryl-1-propenyl)cyclopentanones. Organic Letters, 6(12), 1979-82.
Yoshida M, Sugimoto K, Ihara M. Palladium-catalyzed Ring Expansion Reaction of (Z)-1-(1,3-butadienyl)cyclobutanols With Aryl Iodides. Stereospecific Synthesis of (Z)-2-(3-aryl-1-propenyl)cyclopentanones. Org Lett. 2004 Jun 10;6(12):1979-82. PubMed PMID: 15176798.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Palladium-catalyzed ring expansion reaction of (Z)-1-(1,3-butadienyl)cyclobutanols with aryl iodides. stereospecific synthesis of (Z)-2-(3-aryl-1-propenyl)cyclopentanones. AU - Yoshida,Masahiro, AU - Sugimoto,Kenji, AU - Ihara,Masataka, PY - 2004/6/5/pubmed PY - 2005/4/2/medline PY - 2004/6/5/entrez SP - 1979 EP - 82 JF - Organic letters JO - Org Lett VL - 6 IS - 12 N2 - [reaction: see text] A novel type of cascade ring expansion process has been developed by the palladium-catalyzed reaction of (Z)-1-(1,3-butadienyl)cyclobutanols with aryl iodides. The reaction proceeds in a stereospecific manner to produce (Z)-2-(3-aryl-1-propenyl)cyclopentanones. It has also been found that regioselective alpha-arylation of alkenyl cyclopentanones proceeds to afford the alpha-arylated cyclopentanones. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/15176798/Palladium_catalyzed_ring_expansion_reaction_of__Z__1__13_butadienyl_cyclobutanols_with_aryl_iodides__stereospecific_synthesis_of__Z__2__3_aryl_1_propenyl_cyclopentanones_ DB - PRIME DP - Unbound Medicine ER -