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

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Article information

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

RSC Adv., 2019,9, 23400-23407

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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

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