Palladium(0)-Catalyzed Intermolecular Asymmetric Cascade Dearomatization Reaction of Indoles with Propargyl Carbonate.
Chemistry. 2019 Mar 21; 25(17):4330-4334.C

Abstract

An intermolecular asymmetric cascade dearomatization reaction of indole derivatives with propargyl carbonate was developed. The challenges associated with both the chemoselectivity between the carbon and nitrogen nucleophile and the enantioselective control during the formation of an all-carbon quaternary stereogenic center were well addressed by a Pd catalytic system derived from the Feringa ligand. A series of enantioenriched multiply substituted fused indolenines were provided in good yields (71-86 %) with excellent enantioselectivity (91-96 % ee) and chemoselectivity (3/4>19:1 in most cases).

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Authors+Show Affiliations

Ding L

School of Physical Science and Technology, ShanghaiTech University, 100 Haike Road, Shanghai, 201210, P. R. China.

Gao RD

You SL

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032, P. R. China. School of Physical Science and Technology, ShanghaiTech University, 100 Haike Road, Shanghai, 201210, P. R. China. Collaborative Innovation Center of Chemical Science and Engineering, Tianjin, 300072, P. R. China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

30694590

Citation

Ding, Lu, et al. "Palladium(0)-Catalyzed Intermolecular Asymmetric Cascade Dearomatization Reaction of Indoles With Propargyl Carbonate." Chemistry (Weinheim an Der Bergstrasse, Germany), vol. 25, no. 17, 2019, pp. 4330-4334.

Ding L, Gao RD, You SL. Palladium(0)-Catalyzed Intermolecular Asymmetric Cascade Dearomatization Reaction of Indoles with Propargyl Carbonate. Chemistry. 2019;25(17):4330-4334.

Ding, L., Gao, R. D., & You, S. L. (2019). Palladium(0)-Catalyzed Intermolecular Asymmetric Cascade Dearomatization Reaction of Indoles with Propargyl Carbonate. Chemistry (Weinheim an Der Bergstrasse, Germany), 25(17), 4330-4334. https://doi.org/10.1002/chem.201900425

Ding L, Gao RD, You SL. Palladium(0)-Catalyzed Intermolecular Asymmetric Cascade Dearomatization Reaction of Indoles With Propargyl Carbonate. Chemistry. 2019 Mar 21;25(17):4330-4334. PubMed PMID: 30694590.

* Article titles in AMA citation format should be in sentence-case

TY - JOUR T1 - Palladium(0)-Catalyzed Intermolecular Asymmetric Cascade Dearomatization Reaction of Indoles with Propargyl Carbonate. AU - Ding,Lu, AU - Gao,Run-Duo, AU - You,Shu-Li, Y1 - 2019/02/19/ PY - 2019/01/26/received PY - 2019/1/30/pubmed PY - 2019/1/30/medline PY - 2019/1/30/entrez KW - allylic compounds KW - asymmetric catalysis KW - cascade reactions KW - dearomatization KW - palladium SP - 4330 EP - 4334 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 25 IS - 17 N2 - An intermolecular asymmetric cascade dearomatization reaction of indole derivatives with propargyl carbonate was developed. The challenges associated with both the chemoselectivity between the carbon and nitrogen nucleophile and the enantioselective control during the formation of an all-carbon quaternary stereogenic center were well addressed by a Pd catalytic system derived from the Feringa ligand. A series of enantioenriched multiply substituted fused indolenines were provided in good yields (71-86 %) with excellent enantioselectivity (91-96 % ee) and chemoselectivity (3/4>19:1 in most cases). SN - 1521-3765 UR - https://www.unboundmedicine.com/medline/citation/30694590/Palladium_0__Catalyzed_Intermolecular_Asymmetric_Cascade_Dearomatization_Reaction_of_Indoles_with_Propargyl_Carbonate_ DB - PRIME DP - Unbound Medicine ER -

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Palladium(0)-Catalyzed Intermolecular Asymmetric Cascade Dearomatization Reaction of Indoles with Propargyl Carbonate.Chemistry. 2019 Mar 21; 25(17):4330-4334.C