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. 2019 Jul 29;9(40):23400-23407.
doi: 10.1039/c9ra04889h. eCollection 2019 Jul 23.

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

Makoto Shimizu  1   2 , Miki Mushika  2 , Isao Mizota  2 , Yusong Zhu  1
Affiliations

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

Makoto Shimizu et al. RSC Adv. .

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.

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Conflict of interest statement

There are no conflicts to declare.

Figures

Fig. 1
Fig. 1. Bioactive compounds possessing a quaternary α-amino acid structure.
Scheme 1
Scheme 1. Previous and present works.
Scheme 2
Scheme 2. Reactions in the presence of a radical scavenger or a quencher.
Scheme 3
Scheme 3. Proposed reaction mechanism.
Scheme 4
Scheme 4. Reduction of the diester 4a.
See this image and copyright information in PMC

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