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

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 qu...

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Detalles Bibliográficos
Autores principales: Shimizu, Makoto, Mushika, Miki, Mizota, Isao, Zhu, Yusong
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2019
Materias:
Chemistry
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9067299/
https://www.ncbi.nlm.nih.gov/pubmed/35514493
http://dx.doi.org/10.1039/c9ra04889h
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author Shimizu, Makoto
Mushika, Miki
Mizota, Isao
Zhu, Yusong
author_facet Shimizu, Makoto
Mushika, Miki
Mizota, Isao
Zhu, Yusong
author_sort Shimizu, Makoto
collection PubMed
description 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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spelling pubmed-90672992022-05-04 Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products Shimizu, Makoto Mushika, Miki Mizota, Isao Zhu, Yusong RSC Adv Chemistry 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. The Royal Society of Chemistry 2019-07-29 /pmc/articles/PMC9067299/ /pubmed/35514493 http://dx.doi.org/10.1039/c9ra04889h Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Shimizu, Makoto
Mushika, Miki
Mizota, Isao
Zhu, Yusong
Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products
title Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products
title_full Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products
title_fullStr Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products
title_full_unstemmed Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products
title_short Double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products
title_sort double nucleophilic addition to iminomalonate, leading to the synthesis of quaternary α-amino diesters and desymmetrization of the products
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9067299/
https://www.ncbi.nlm.nih.gov/pubmed/35514493
http://dx.doi.org/10.1039/c9ra04889h
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AT mizotaisao doublenucleophilicadditiontoiminomalonateleadingtothesynthesisofquaternaryaaminodiestersanddesymmetrizationoftheproducts
AT zhuyusong doublenucleophilicadditiontoiminomalonateleadingtothesynthesisofquaternaryaaminodiestersanddesymmetrizationoftheproducts

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