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Silica-immobilized chiral dirhodium(II) catalyst for enantioselective carbenoid reactions.
Org Lett. 2013 Dec 20; 15(24):6136-9.OL

Abstract

A silica-supported dirhodium(II) tetraprolinate catalyst was synthesized in four steps from l-proline and used in a range of enantioselective transformations of donor/acceptor carbenoids. These include cyclopropenation, cyclopropanation, tandem ylide formation/[2,3] sigmatropic rearrangement, and a variety of combined C-H functionalization/Cope rearrangement reactions. The products of these transformations were obtained in yields and levels of enantioselectivity comparable to those obtained with its homogeneous counterpart, Rh2(S-DOSP)4. The silica-supported Rh2(S-DOSP)4 derivative was successfully recycled over five reactions.

Authors+Show Affiliations

Department of Chemistry, Emory University , 1515 Dickey Drive, Atlanta, Georgia 30322, United States , and School of Chemical & Biomolecular Engineering, Georgia Institute of Technology , 311 Ferst Drive, Atlanta, Georgia 30322, United States.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

24251986

Citation

Chepiga, Kathryn M., et al. "Silica-immobilized Chiral dirhodium(II) Catalyst for Enantioselective Carbenoid Reactions." Organic Letters, vol. 15, no. 24, 2013, pp. 6136-9.
Chepiga KM, Feng Y, Brunelli NA, et al. Silica-immobilized chiral dirhodium(II) catalyst for enantioselective carbenoid reactions. Org Lett. 2013;15(24):6136-9.
Chepiga, K. M., Feng, Y., Brunelli, N. A., Jones, C. W., & Davies, H. M. (2013). Silica-immobilized chiral dirhodium(II) catalyst for enantioselective carbenoid reactions. Organic Letters, 15(24), 6136-9. https://doi.org/10.1021/ol403006r
Chepiga KM, et al. Silica-immobilized Chiral dirhodium(II) Catalyst for Enantioselective Carbenoid Reactions. Org Lett. 2013 Dec 20;15(24):6136-9. PubMed PMID: 24251986.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Silica-immobilized chiral dirhodium(II) catalyst for enantioselective carbenoid reactions. AU - Chepiga,Kathryn M, AU - Feng,Yan, AU - Brunelli,Nicholas A, AU - Jones,Christopher W, AU - Davies,Huw M L, Y1 - 2013/11/19/ PY - 2013/11/21/entrez PY - 2013/11/21/pubmed PY - 2014/2/25/medline SP - 6136 EP - 9 JF - Organic letters JO - Org Lett VL - 15 IS - 24 N2 - A silica-supported dirhodium(II) tetraprolinate catalyst was synthesized in four steps from l-proline and used in a range of enantioselective transformations of donor/acceptor carbenoids. These include cyclopropenation, cyclopropanation, tandem ylide formation/[2,3] sigmatropic rearrangement, and a variety of combined C-H functionalization/Cope rearrangement reactions. The products of these transformations were obtained in yields and levels of enantioselectivity comparable to those obtained with its homogeneous counterpart, Rh2(S-DOSP)4. The silica-supported Rh2(S-DOSP)4 derivative was successfully recycled over five reactions. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/24251986/Silica_immobilized_chiral_dirhodium_II__catalyst_for_enantioselective_carbenoid_reactions_ DB - PRIME DP - Unbound Medicine ER -