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Stereoselective synthesis of vinyl-substituted (Z)-stilbenes by rhodium-catalysed addition of arylboronic acids to allenic alcohols.
Org Biomol Chem. 2010 Sep 21; 8(18):4074-6.OB

Abstract

Vinyl-substituted (Z)-stilbenes are stereoselectively synthesised on treatment of 4-arylbuta-2,3-dien-1-ols with arylboronic acids in the presence of a rhodium(i) catalyst. The reaction proceeds through the regioselective addition of organorhodium(i) species across the aryl-substituted carbon-carbon double bond of the allene moiety and subsequent delta-elimination of Rh(i)-OH.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Miura T
Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan. murakami@sbchem.kyoto-u.ac.
Shimizu H
No affiliation info available
Igarashi T
No affiliation info available
Murakami M
No affiliation info available

MeSH

AlcoholsAlkadienesBoronic AcidsCatalysisMolecular StructureOrganometallic CompoundsRhodiumStereoisomerismStilbenes

Pub Type(s)

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

Language

eng

PubMed ID

20661491

Citation

Miura, Tomoya, et al. "Stereoselective Synthesis of Vinyl-substituted (Z)-stilbenes By Rhodium-catalysed Addition of Arylboronic Acids to Allenic Alcohols." Organic & Biomolecular Chemistry, vol. 8, no. 18, 2010, pp. 4074-6.
Miura T, Shimizu H, Igarashi T, et al. Stereoselective synthesis of vinyl-substituted (Z)-stilbenes by rhodium-catalysed addition of arylboronic acids to allenic alcohols. Org Biomol Chem. 2010;8(18):4074-6.
Miura, T., Shimizu, H., Igarashi, T., & Murakami, M. (2010). Stereoselective synthesis of vinyl-substituted (Z)-stilbenes by rhodium-catalysed addition of arylboronic acids to allenic alcohols. Organic & Biomolecular Chemistry, 8(18), 4074-6. https://doi.org/10.1039/c0ob00163e
Miura T, et al. Stereoselective Synthesis of Vinyl-substituted (Z)-stilbenes By Rhodium-catalysed Addition of Arylboronic Acids to Allenic Alcohols. Org Biomol Chem. 2010 Sep 21;8(18):4074-6. PubMed PMID: 20661491.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Stereoselective synthesis of vinyl-substituted (Z)-stilbenes by rhodium-catalysed addition of arylboronic acids to allenic alcohols. AU - Miura,Tomoya, AU - Shimizu,Hiroshi, AU - Igarashi,Tomohiro, AU - Murakami,Masahiro, Y1 - 2010/07/26/ PY - 2010/7/28/entrez PY - 2010/7/28/pubmed PY - 2010/12/14/medline SP - 4074 EP - 6 JF - Organic & biomolecular chemistry JO - Org Biomol Chem VL - 8 IS - 18 N2 - Vinyl-substituted (Z)-stilbenes are stereoselectively synthesised on treatment of 4-arylbuta-2,3-dien-1-ols with arylboronic acids in the presence of a rhodium(i) catalyst. The reaction proceeds through the regioselective addition of organorhodium(i) species across the aryl-substituted carbon-carbon double bond of the allene moiety and subsequent delta-elimination of Rh(i)-OH. SN - 1477-0539 UR - https://www.unboundmedicine.com/medline/citation/20661491/Stereoselective_synthesis_of_vinyl_substituted__Z__stilbenes_by_rhodium_catalysed_addition_of_arylboronic_acids_to_allenic_alcohols_ L2 - https://doi.org/10.1039/c0ob00163e DB - PRIME DP - Unbound Medicine ER -