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A rhodium(I)-catalyzed demethylation-cyclization of o-anisole-substituted ynamides in the synthesis of chiral 2-amido benzofurans.
Org Lett. 2007 Jun 07; 9(12):2361-4.OL

Abstract

A Rh(I)-catalyzed demethylation-cyclization sequence for a direct transformation of o-anisole-substituted ynamides to benzofurans is described here. The Ag salt functions synergistically with Rh(I) for the key demethylation step.

Authors+Show Affiliations

Oppenheimer J
Division of Pharmaceutical Sciencies and Department of Chemistry, University of Wisconsin-Madison, Rennebohm Hall, 777 Highland Avenue, Madison, Wisconsin 53705-2222, USA.
Johnson WL
No affiliation info available
Tracey MR
No affiliation info available
Hsung RP
No affiliation info available
Yao PY
No affiliation info available
Liu R
No affiliation info available
Zhao K
No affiliation info available

MeSH

AlkynesAmidesAnisolesBenzofuransCatalysisCrystallography, X-RayCyclizationMethylationModels, MolecularMolecular StructureOrganometallic CompoundsRhodiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

17489599

Citation

Oppenheimer, Jossian, et al. "A rhodium(I)-catalyzed Demethylation-cyclization of O-anisole-substituted Ynamides in the Synthesis of Chiral 2-amido Benzofurans." Organic Letters, vol. 9, no. 12, 2007, pp. 2361-4.
Oppenheimer J, Johnson WL, Tracey MR, et al. A rhodium(I)-catalyzed demethylation-cyclization of o-anisole-substituted ynamides in the synthesis of chiral 2-amido benzofurans. Org Lett. 2007;9(12):2361-4.
Oppenheimer, J., Johnson, W. L., Tracey, M. R., Hsung, R. P., Yao, P. Y., Liu, R., & Zhao, K. (2007). A rhodium(I)-catalyzed demethylation-cyclization of o-anisole-substituted ynamides in the synthesis of chiral 2-amido benzofurans. Organic Letters, 9(12), 2361-4.
Oppenheimer J, et al. A rhodium(I)-catalyzed Demethylation-cyclization of O-anisole-substituted Ynamides in the Synthesis of Chiral 2-amido Benzofurans. Org Lett. 2007 Jun 7;9(12):2361-4. PubMed PMID: 17489599.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - A rhodium(I)-catalyzed demethylation-cyclization of o-anisole-substituted ynamides in the synthesis of chiral 2-amido benzofurans. AU - Oppenheimer,Jossian, AU - Johnson,Whitney L, AU - Tracey,Michael R, AU - Hsung,Richard P, AU - Yao,Pei-Yuan, AU - Liu,Renhe, AU - Zhao,Kang, Y1 - 2007/05/10/ PY - 2007/5/11/pubmed PY - 2007/8/19/medline PY - 2007/5/11/entrez SP - 2361 EP - 4 JF - Organic letters JO - Org Lett VL - 9 IS - 12 N2 - A Rh(I)-catalyzed demethylation-cyclization sequence for a direct transformation of o-anisole-substituted ynamides to benzofurans is described here. The Ag salt functions synergistically with Rh(I) for the key demethylation step. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/17489599/A_rhodium_I__catalyzed_demethylation_cyclization_of_o_anisole_substituted_ynamides_in_the_synthesis_of_chiral_2_amido_benzofurans_ L2 - https://doi.org/10.1021/ol0707362 DB - PRIME DP - Unbound Medicine ER -