Asymmetric Friedel-Crafts-Type Reaction of 2-Vinylindoles to N-Boc Imines Using a Chiral Imidazolidine-Containing NCN-Pincer Pd Catalyst

Tomoya Yokota; Hyuma Masu; Takayoshi Arai

doi:10.1021/acs.joc.2c02911

Asymmetric Friedel-Crafts-Type Reaction of 2-Vinylindoles to N-Boc Imines Using a Chiral Imidazolidine-Containing NCN-Pincer Pd Catalyst

J Org Chem. 2023 Jun 16;88(12):7872-7881. doi: 10.1021/acs.joc.2c02911. Epub 2023 Feb 20.

Authors

Tomoya Yokota¹, Hyuma Masu², Takayoshi Arai¹

Affiliations

¹ Soft Molecular Activation Research Center (SMARC), Chiba Iodine Resource Innovation Center (CIRIC), Synthetic Organic Chemistry, Department of Chemistry, Graduate School of Science, Chiba University, 1-33 Yayoi, Inage, Chiba, Chiba 263-8522, Japan.
² Center for Analytical Instrumentation, Chiba University, 1-33 Yayoi, Inage, Chiba, Chiba 263-8522, Japan.

PMID: 36802597
DOI: 10.1021/acs.joc.2c02911

Abstract

A chiral imidazolidine-containing NCN-pincer Pd-OTf complex (NCN-Pd cat) promoted the asymmetric nucleophilic addition of unprotected 2-vinylindoles to N-Boc imines in a Friedel-Crafts-type manner. The chiral (2-vinyl-1H-indol-3-yl)methanamine products become nice platforms for constructing multiple ring systems.

MeSH terms

Imidazolidines*
Imines
Indoles*
Molecular Structure
Stereoisomerism

Substances

Indoles
Imines
Imidazolidines