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Catalytic asymmetric synthesis of pyrroloindolines via a rhodium(II)-catalyzed annulation of indoles.
J Am Chem Soc. 2013 May 08; 135(18):6802-5.JA

Abstract

Herein we report the synthesis of pyrroloindolines via a catalytic enantioselective formal [3+2] cycloaddition of C(3)-substituted indoles. This methodology utilizes 4-aryl-1-sulfonyl-1,2,3-triazoles as carbenoid precursors and the rhodium(II)-tetracarboxylate catalyst Rh2(S-PTAD)4. A variety of aryl-substituted pyrroloindolines were prepared in good yields and with high levels of enantioinduction.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Spangler JE
Department of Chemistry, Emory University, Atlanta, Georgia 30322, United States.
Davies HM
No affiliation info available

MeSH

CatalysisIndolesMolecular StructureOrganometallic CompoundsPyrrolesRhodiumStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

23607705

Citation

Spangler, Jillian E., and Huw M L. Davies. "Catalytic Asymmetric Synthesis of Pyrroloindolines Via a rhodium(II)-catalyzed Annulation of Indoles." Journal of the American Chemical Society, vol. 135, no. 18, 2013, pp. 6802-5.
Spangler JE, Davies HM. Catalytic asymmetric synthesis of pyrroloindolines via a rhodium(II)-catalyzed annulation of indoles. J Am Chem Soc. 2013;135(18):6802-5.
Spangler, J. E., & Davies, H. M. (2013). Catalytic asymmetric synthesis of pyrroloindolines via a rhodium(II)-catalyzed annulation of indoles. Journal of the American Chemical Society, 135(18), 6802-5. https://doi.org/10.1021/ja4025337
Spangler JE, Davies HM. Catalytic Asymmetric Synthesis of Pyrroloindolines Via a rhodium(II)-catalyzed Annulation of Indoles. J Am Chem Soc. 2013 May 8;135(18):6802-5. PubMed PMID: 23607705.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Catalytic asymmetric synthesis of pyrroloindolines via a rhodium(II)-catalyzed annulation of indoles. AU - Spangler,Jillian E, AU - Davies,Huw M L, Y1 - 2013/04/30/ PY - 2013/4/24/entrez PY - 2013/4/24/pubmed PY - 2013/12/16/medline SP - 6802 EP - 5 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 135 IS - 18 N2 - Herein we report the synthesis of pyrroloindolines via a catalytic enantioselective formal [3+2] cycloaddition of C(3)-substituted indoles. This methodology utilizes 4-aryl-1-sulfonyl-1,2,3-triazoles as carbenoid precursors and the rhodium(II)-tetracarboxylate catalyst Rh2(S-PTAD)4. A variety of aryl-substituted pyrroloindolines were prepared in good yields and with high levels of enantioinduction. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/23607705/Catalytic_asymmetric_synthesis_of_pyrroloindolines_via_a_rhodium_II__catalyzed_annulation_of_indoles_ L2 - https://doi.org/10.1021/ja4025337 DB - PRIME DP - Unbound Medicine ER -