Issue 24, 2021
From the journal:

Organic Chemistry Frontiers

Cp*Ir(iii)/chiral carboxylic acid-catalyzed enantioselective C–H alkylation of ferrocene carboxamides with diazomalonates†

Qi Mou,a   Ruyuan Zhao,a   Ruihan Niu,a   Seiya Fukagawa,b   Taiki Shigeno,b   Tatsuhiko Yoshino, ORCID logo bc   Shigeki Matsunaga ORCID logo *bc  and  Bo Sun ORCID logo *a  

* Corresponding authors

a State Key Laboratory Base of Eco-chemical Engineering, College of Chemical Engineering, Qingdao University of Science & Technology, Qingdao 266042, P. R. China
E-mail: sun0109@qust.edu.cn

b Faculty of Pharmaceutical Science, Hokkaido University, Sapporo 060-0812, Japan
E-mail: smatsuna@pharm.hokudai.ac.jp

c Global Station for Biosurfaces and Drug Discovery, Hokkaido University, Sapporo 060-0812, Japan

Abstract

Enantioselective C–H alkylation of ferrocene carboxamides with diazomalonates using an achiral Cp*Ir(III)/chiral carboxylic acid is described. The combination of an achiral Cp*Ir(III) complex and a binaphthyl-based chiral carboxylic acid provided planar chiral alkylated ferrocenes in good yields with moderate to good enantioselectivity (up to 94 : 6 er).

Graphical abstract: Cp*Ir(iii)/chiral carboxylic acid-catalyzed enantioselective C–H alkylation of ferrocene carboxamides with diazomalonates

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Article information

DOI
https://doi.org/10.1039/D1QO01344K
Article type
Research Article
Submitted
09 Sep 2021
Accepted
22 Oct 2021
First published
26 Oct 2021

Org. Chem. Front., 2021,8, 6923-6930

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Cp*Ir(III)/chiral carboxylic acid-catalyzed enantioselective C–H alkylation of ferrocene carboxamides with diazomalonates

Q. Mou, R. Zhao, R. Niu, S. Fukagawa, T. Shigeno, T. Yoshino, S. Matsunaga and B. Sun, Org. Chem. Front., 2021, 8, 6923 DOI: 10.1039/D1QO01344K

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