Issue 6, 2021
From the journal:

Organic Chemistry Frontiers

Constructing chiral aza-quaternary carbon centers by enantioselective carbonylative Heck reaction of o-iodoanilines with allenes†

Zhengshuai Xu,a   Chaoren Shen, ORCID logo a   Hongru Zhang,a   Peng Wanga  and  Kaiwu Dong ORCID logo *a  

* Corresponding authors

a Chang-Kung Chuang Institute, Shanghai Key Laboratory of Green Chemistry and Chemical Process, School of Chemistry and Molecular Engineering, East China Normal University, Shanghai 200241, China
E-mail: kwdong@chem.ecnu.edu.cn

Abstract

The construction of chiral aza-quaternary carbon centers via C–N bond formation has been achieved by a palladium-catalyzed asymmetric carbonylative Heck reaction of o-iodoanilines with allenes, providing chiral dihydroquinolinone derivatives with moderate to high yield and enantiomeric ratio (er). The er could be improved to 99/1 through the recrystallization of the isolated products. Adding o-iodoaniline into the reaction by syringe pump was crucial to diminish the side reactions of reactive o-iodoanilines and improve the chemoselectivity. Utilizing the chirality induction of an assembled aza-quaternary stereogenic center, molecules bearing vicinal chiral quaternary carbon centers or multiple chiral centers can be rapidly prepared.

Graphical abstract: Constructing chiral aza-quaternary carbon centers by enantioselective carbonylative Heck reaction of o-iodoanilines with allenes

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Article information

DOI
https://doi.org/10.1039/D0QO01486A
Article type
Research Article
Submitted
26 Nov 2020
Accepted
29 Dec 2020
First published
30 Dec 2020

Org. Chem. Front., 2021,8, 1163-1169

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Constructing chiral aza-quaternary carbon centers by enantioselective carbonylative Heck reaction of o-iodoanilines with allenes

Z. Xu, C. Shen, H. Zhang, P. Wang and K. Dong, Org. Chem. Front., 2021, 8, 1163 DOI: 10.1039/D0QO01486A

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