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

Makoto Shimizu; Miki Mushika; Isao Mizota; Yusong Zhu

doi:10.1039/c9ra04889h

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

Makoto Shimizu, Miki Mushika, Isao Mizota, Yusong Zhu

School of energy science and engineering

Research output: Contribution to journal › Article › peer-review

13 Scopus citations

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.

Original language	English
Pages (from-to)	23400-23407
Number of pages	8
Journal	RSC Advances
Volume	9
Issue number	40
DOIs	https://doi.org/10.1039/c9ra04889h
State	Published - 2019

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title = "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.",

author = "Makoto Shimizu and Miki Mushika and Isao Mizota and Yusong Zhu",

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AU - Shimizu, Makoto

AU - Mushika, Miki

AU - Mizota, Isao

AU - Zhu, Yusong

PY - 2019

Y1 - 2019

N2 - 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.

AB - 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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U2 - 10.1039/c9ra04889h

DO - 10.1039/c9ra04889h

M3 - 文章

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SN - 2046-2069

VL - 9

SP - 23400

EP - 23407

JO - RSC Advances

JF - RSC Advances

IS - 40

ER -

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

Abstract

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