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Enantioselective Rh-catalyzed domino transformations of alkynylcyclohexadienones with organoboron reagents.
Org Lett. 2013 Mar 01; 15(5):1148-51.OL

Abstract

A new enantioselective rhodium-catalyzed domino reaction is described that gives access to fused heterocycles by desymmetrization of alkyne-tethered cyclohexadienones. Two new C-C bonds and two stereocenters are formed in one step with good enantioselectivity. In contrast to prior reports, it was found that a vinylidene is not involved in the product formation but that syn-addition of the rhodium-aryl species onto the alkyne takes place.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Keilitz J
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, Ontario M5S 3H6, Canada.
Newman SG
No affiliation info available
Lautens M
No affiliation info available

MeSH

AlkynesBoron CompoundsCatalysisCyclohexanesHeterocyclic CompoundsIndicators and ReagentsMolecular StructureRhodiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

23421491

Citation

Keilitz, Juliane, et al. "Enantioselective Rh-catalyzed Domino Transformations of Alkynylcyclohexadienones With Organoboron Reagents." Organic Letters, vol. 15, no. 5, 2013, pp. 1148-51.
Keilitz J, Newman SG, Lautens M. Enantioselective Rh-catalyzed domino transformations of alkynylcyclohexadienones with organoboron reagents. Org Lett. 2013;15(5):1148-51.
Keilitz, J., Newman, S. G., & Lautens, M. (2013). Enantioselective Rh-catalyzed domino transformations of alkynylcyclohexadienones with organoboron reagents. Organic Letters, 15(5), 1148-51. https://doi.org/10.1021/ol400363f
Keilitz J, Newman SG, Lautens M. Enantioselective Rh-catalyzed Domino Transformations of Alkynylcyclohexadienones With Organoboron Reagents. Org Lett. 2013 Mar 1;15(5):1148-51. PubMed PMID: 23421491.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective Rh-catalyzed domino transformations of alkynylcyclohexadienones with organoboron reagents. AU - Keilitz,Juliane, AU - Newman,Stephen G, AU - Lautens,Mark, Y1 - 2013/02/20/ PY - 2013/2/21/entrez PY - 2013/2/21/pubmed PY - 2013/7/3/medline SP - 1148 EP - 51 JF - Organic letters JO - Org Lett VL - 15 IS - 5 N2 - A new enantioselective rhodium-catalyzed domino reaction is described that gives access to fused heterocycles by desymmetrization of alkyne-tethered cyclohexadienones. Two new C-C bonds and two stereocenters are formed in one step with good enantioselectivity. In contrast to prior reports, it was found that a vinylidene is not involved in the product formation but that syn-addition of the rhodium-aryl species onto the alkyne takes place. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/23421491/Enantioselective_Rh_catalyzed_domino_transformations_of_alkynylcyclohexadienones_with_organoboron_reagents_ L2 - https://doi.org/10.1021/ol400363f DB - PRIME DP - Unbound Medicine ER -