Tags

Type your tag names separated by a space and hit enter

Enantioselective functionalization of indoles and pyrroles via an in situ-formed spiro intermediate.
J Am Chem Soc. 2013 Jun 05; 135(22):8169-72.JA

Abstract

Herein we report a highly enantioselective synthesis of polycyclic indoles and pyrroles with up to 99% ee by an iridium catalyst system consisting of a commercially available iridium precursor and a readily accessible ligand. Investigation of the reaction mechanism led to the discovery of an unprecedented dearomatized spiro intermediate and its in situ migration phenomenon. The new reaction mode features switching of the substituent from the indole C-3 position to the C-2 position (from the C-2 position to the C-3 position in the case of pyrrole) without loss of the enantiomeric purity, providing a novel concept in designing the asymmetric construction of enantiopure polycyclic indoles and pyrroles.

Links

Publisher Full Text (DOI)

Authors+Show Affiliations

Zhuo CX
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry , Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China.
Wu QF
No affiliation info available
Zhao Q
No affiliation info available
Xu QL
No affiliation info available
You SL
No affiliation info available

MeSH

CatalysisIndolesIridiumMolecular StructureOrganometallic CompoundsPyrrolesSpiro CompoundsStereoisomerism

Pub Type(s)

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

Language

eng

PubMed ID

23672506

Citation

Zhuo, Chun-Xiang, et al. "Enantioselective Functionalization of Indoles and Pyrroles Via an in Situ-formed Spiro Intermediate." Journal of the American Chemical Society, vol. 135, no. 22, 2013, pp. 8169-72.
Zhuo CX, Wu QF, Zhao Q, et al. Enantioselective functionalization of indoles and pyrroles via an in situ-formed spiro intermediate. J Am Chem Soc. 2013;135(22):8169-72.
Zhuo, C. X., Wu, Q. F., Zhao, Q., Xu, Q. L., & You, S. L. (2013). Enantioselective functionalization of indoles and pyrroles via an in situ-formed spiro intermediate. Journal of the American Chemical Society, 135(22), 8169-72. https://doi.org/10.1021/ja403535a
Zhuo CX, et al. Enantioselective Functionalization of Indoles and Pyrroles Via an in Situ-formed Spiro Intermediate. J Am Chem Soc. 2013 Jun 5;135(22):8169-72. PubMed PMID: 23672506.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Enantioselective functionalization of indoles and pyrroles via an in situ-formed spiro intermediate. AU - Zhuo,Chun-Xiang, AU - Wu,Qing-Feng, AU - Zhao,Qiang, AU - Xu,Qing-Long, AU - You,Shu-Li, Y1 - 2013/05/20/ PY - 2013/5/16/entrez PY - 2013/5/16/pubmed PY - 2014/10/1/medline SP - 8169 EP - 72 JF - Journal of the American Chemical Society JO - J Am Chem Soc VL - 135 IS - 22 N2 - Herein we report a highly enantioselective synthesis of polycyclic indoles and pyrroles with up to 99% ee by an iridium catalyst system consisting of a commercially available iridium precursor and a readily accessible ligand. Investigation of the reaction mechanism led to the discovery of an unprecedented dearomatized spiro intermediate and its in situ migration phenomenon. The new reaction mode features switching of the substituent from the indole C-3 position to the C-2 position (from the C-2 position to the C-3 position in the case of pyrrole) without loss of the enantiomeric purity, providing a novel concept in designing the asymmetric construction of enantiopure polycyclic indoles and pyrroles. SN - 1520-5126 UR - https://www.unboundmedicine.com/medline/citation/23672506/Enantioselective_functionalization_of_indoles_and_pyrroles_via_an_in_situ_formed_spiro_intermediate_ L2 - https://doi.org/10.1021/ja403535a DB - PRIME DP - Unbound Medicine ER -