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Rh(2)(S-PTTL)(3)TPA-A Mixed Ligand Dirhodium(II) Catalyst for Enantioselective Reactions of α-Alkyl-α-Diazoesters.
Chem Sci. 2012 May; 3(5):1589-1593.CS

Abstract

Herein we report the synthesis of the mixed ligand paddlewheel complex dirhodium(II) tris[N-phthaloyl-(S)-tert-leucinate] triphenylacetate, Rh(2)(S-PTTL)(3)TPA, the structure of which bears similarity to the chiral crown complex Rh(2)(S-PTTL)(4). Rh(2)(S-PTTL)(3)TPA engages substrate classes (aliphatic alkynes, silylacetylenes, α-olefins) that are especially challenging in intermolecular reactions of α-alkyl-α-diazoesters, and catalyzes enantioselective cyclopropanation, cyclopropenation, and indole C-H functionalization with yields and enantioselectivities that are comparable or superior to Rh(2)(S-PTTL)(4). Mixing ligands on paddlewheel complexes offers a versatile handle for diversifying catalyst structure and reactivity. The results described herein illustrate how mixed ligand catalysts can create new opportunities for the optimization of catalytic asymmetric processes.

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Authors+Show Affiliations

Boruta DT
Brown Laboratory, Department of Chemistry and Biochemistry, Newark, DE 19803, USA. ; Tel: +1 302 831 0191.
Dmitrenko O
No affiliation info available
Yap GP
No affiliation info available
Fox JM
No affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

23125912

Citation

Boruta, David T., et al. "Rh(2)(S-PTTL)(3)TPA-A Mixed Ligand Dirhodium(II) Catalyst for Enantioselective Reactions of Α-Alkyl-α-Diazoesters." Chemical Science, vol. 3, no. 5, 2012, pp. 1589-1593.
Boruta DT, Dmitrenko O, Yap GP, et al. Rh(2)(S-PTTL)(3)TPA-A Mixed Ligand Dirhodium(II) Catalyst for Enantioselective Reactions of α-Alkyl-α-Diazoesters. Chem Sci. 2012;3(5):1589-1593.
Boruta, D. T., Dmitrenko, O., Yap, G. P., & Fox, J. M. (2012). Rh(2)(S-PTTL)(3)TPA-A Mixed Ligand Dirhodium(II) Catalyst for Enantioselective Reactions of α-Alkyl-α-Diazoesters. Chemical Science, 3(5), 1589-1593.
Boruta DT, et al. Rh(2)(S-PTTL)(3)TPA-A Mixed Ligand Dirhodium(II) Catalyst for Enantioselective Reactions of Α-Alkyl-α-Diazoesters. Chem Sci. 2012;3(5):1589-1593. PubMed PMID: 23125912.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Rh(2)(S-PTTL)(3)TPA-A Mixed Ligand Dirhodium(II) Catalyst for Enantioselective Reactions of α-Alkyl-α-Diazoesters. AU - Boruta,David T, AU - Dmitrenko,Olga, AU - Yap,Glenn P A, AU - Fox,Joseph M, PY - 2012/11/6/entrez PY - 2012/11/6/pubmed PY - 2012/11/6/medline SP - 1589 EP - 1593 JF - Chemical science JO - Chem Sci VL - 3 IS - 5 N2 - Herein we report the synthesis of the mixed ligand paddlewheel complex dirhodium(II) tris[N-phthaloyl-(S)-tert-leucinate] triphenylacetate, Rh(2)(S-PTTL)(3)TPA, the structure of which bears similarity to the chiral crown complex Rh(2)(S-PTTL)(4). Rh(2)(S-PTTL)(3)TPA engages substrate classes (aliphatic alkynes, silylacetylenes, α-olefins) that are especially challenging in intermolecular reactions of α-alkyl-α-diazoesters, and catalyzes enantioselective cyclopropanation, cyclopropenation, and indole C-H functionalization with yields and enantioselectivities that are comparable or superior to Rh(2)(S-PTTL)(4). Mixing ligands on paddlewheel complexes offers a versatile handle for diversifying catalyst structure and reactivity. The results described herein illustrate how mixed ligand catalysts can create new opportunities for the optimization of catalytic asymmetric processes. SN - 2041-6520 UR - https://www.unboundmedicine.com/medline/citation/23125912/Rh_2__S_PTTL__3_TPA_A_Mixed_Ligand_Dirhodium_II__Catalyst_for_Enantioselective_Reactions_of_α_Alkyl_α_Diazoesters_ L2 - https://doi.org/10.1039/C2SC01134D DB - PRIME DP - Unbound Medicine ER -