Issue 40, 2019

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

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

Supplementary files

Article information

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

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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