Issue 40, 2019
From the journal:

RSC Advances

Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products†

Makoto Shimizu, ORCID logo *ab   Miki Mushika,b   Isao Mizotab  and  Yusong Zhua  

* Corresponding authors

a School of Energy Science and Engineering, Nanjing Tech University, Nanjing 211816, Jiangsu Province, China

b Department of Chemistry for Materials, Graduate School of Engineering, Mie University, Tsu, Mie 514-8507, Japan
E-mail: mshimizu@chem.mie-u.ac.jp

Abstract

Alkylation of iminomalonate with Grignard reagents followed by oxidation and allylation gave symmetrical quaternary α-amino diesters in good yields. Subsequent desymmetrization of a diol derivative from these products was conducted via asymmetric carbamylation catalyzed by Cu-Bnbox to give chiral quaternary aminodiol mono-carbamates.

Graphical abstract: Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C9RA04889H
Article type
Paper
Submitted
28 jun 2019
Accepted
22 jul 2019
First published
29 jul 2019
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2019,9, 23400-23407

Permissions

Request permissions

Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products

M. Shimizu, M. Mushika, I. Mizota and Y. Zhu, RSC Adv., 2019, 9, 23400 DOI: 10.1039/C9RA04889H

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements