Chiral Phosphoric Acid-Catalyzed Enantioselective Aza-Friedel-Crafts Addition of Naphthols with Isatin-Derived Ketimines

Mei Duan; Jingchao Chen; Ting Wang; Shaojian Luo; Meifen Wang; Baomin Fan

doi:10.1021/acs.joc.2c01659

Chiral Phosphoric Acid-Catalyzed Enantioselective Aza-Friedel-Crafts Addition of Naphthols with Isatin-Derived Ketimines

J Org Chem. 2022 Nov 18;87(22):15152-15158. doi: 10.1021/acs.joc.2c01659. Epub 2022 Oct 21.

Authors

Mei Duan¹, Jingchao Chen¹, Ting Wang¹, Shaojian Luo¹, Meifen Wang¹, Baomin Fan^{1

2}

Affiliations

¹ Key Laboratory of Chemistry in Ethnic Medicinal Resources (Yunnan Minzu University), State Ethnic Affairs Commission & Ministry of Education, Yunnan Minzu University, Kunming650504, Yunnan, China.
² Department School of Chemistry and Environment, Yunnan Minzu University, Kunming650504, Yunnan, China.

PMID: 36269152
DOI: 10.1021/acs.joc.2c01659

Abstract

The enantioselective Friedel-Crafts addition of naphthols with isatin-derived ketimines was developed with H₈-BINOL-derived chiral biaryl phosphoric acid. A wide range of isatin-derived ketimines and naphthols were successfully applied and gave a series of chiral 3-amino-2-oxindoles in excellent yields with high optical purities.

Publication types

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

MeSH terms

Catalysis
Isatin*
Molecular Structure
Naphthols
Stereoisomerism

Substances

ketimine
Isatin
phosphoric acid
Naphthols