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Rh-catalyzed intermolecular cyclopropanation with alpha-alkyl-alpha-diazoesters: catalyst-dependent chemo- and diastereoselectivity.
Org Lett. 2008 Jul 17; 10(14):2987-9.OL

Abstract

A Rh-catalyzed procedure for the cyclopropanation of alkenes with alpha-alkyl-alpha-diazoesters is described. With dirhodium tetraoctanoate, the predominant pathway is beta-hydride elimination. While a number of sterically demanding carboxylate ligands serve to avoid beta-hydride elimination, it was found that triphenylacetate (TPA) also imparts high diastereoselectivity.

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Authors+Show Affiliations

Panne P
Brown Laboratories, Department of Chemistry and Biochemistry, University of Delaware, Newark, Delaware 19716, USA.
DeAngelis A
No affiliation info available
Fox JM
No affiliation info available

MeSH

AlkenesAzo CompoundsCatalysisEstersRhodiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

18547051

Citation

Panne, Patricia, et al. "Rh-catalyzed Intermolecular Cyclopropanation With Alpha-alkyl-alpha-diazoesters: Catalyst-dependent Chemo- and Diastereoselectivity." Organic Letters, vol. 10, no. 14, 2008, pp. 2987-9.
Panne P, DeAngelis A, Fox JM. Rh-catalyzed intermolecular cyclopropanation with alpha-alkyl-alpha-diazoesters: catalyst-dependent chemo- and diastereoselectivity. Org Lett. 2008;10(14):2987-9.
Panne, P., DeAngelis, A., & Fox, J. M. (2008). Rh-catalyzed intermolecular cyclopropanation with alpha-alkyl-alpha-diazoesters: catalyst-dependent chemo- and diastereoselectivity. Organic Letters, 10(14), 2987-9. https://doi.org/10.1021/ol800983y
Panne P, DeAngelis A, Fox JM. Rh-catalyzed Intermolecular Cyclopropanation With Alpha-alkyl-alpha-diazoesters: Catalyst-dependent Chemo- and Diastereoselectivity. Org Lett. 2008 Jul 17;10(14):2987-9. PubMed PMID: 18547051.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rh-catalyzed intermolecular cyclopropanation with alpha-alkyl-alpha-diazoesters: catalyst-dependent chemo- and diastereoselectivity. AU - Panne,Patricia, AU - DeAngelis,Andrew, AU - Fox,Joseph M, Y1 - 2008/06/12/ PY - 2008/6/13/pubmed PY - 2008/9/18/medline PY - 2008/6/13/entrez SP - 2987 EP - 9 JF - Organic letters JO - Org Lett VL - 10 IS - 14 N2 - A Rh-catalyzed procedure for the cyclopropanation of alkenes with alpha-alkyl-alpha-diazoesters is described. With dirhodium tetraoctanoate, the predominant pathway is beta-hydride elimination. While a number of sterically demanding carboxylate ligands serve to avoid beta-hydride elimination, it was found that triphenylacetate (TPA) also imparts high diastereoselectivity. SN - 1523-7060 UR - https://www.unboundmedicine.com/medline/citation/18547051/Rh_catalyzed_intermolecular_cyclopropanation_with_alpha_alkyl_alpha_diazoesters:_catalyst_dependent_chemo__and_diastereoselectivity_ L2 - https://doi.org/10.1021/ol800983y DB - PRIME DP - Unbound Medicine ER -