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Diastereoselective radical addition to γ-alkyl-α-methylene-γ-butyrolactams and the synthesis of a chiral pyroglutamic acid derivative

The cis- and trans-stereoselective radical additions to α-methylene-γ-alkyl- γ-lactams were investigated and the scope and limitation of the reaction were also revealed. This stereoselective radical reaction was used for synthesis of chiral pyroglutamic acid derivatives starting from a commercially...

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Autores principales: Yajima, Tomoko, Yoshida, Eriko, Hamano, Masako
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3740493/
https://www.ncbi.nlm.nih.gov/pubmed/23946839
http://dx.doi.org/10.3762/bjoc.9.161
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author Yajima, Tomoko
Yoshida, Eriko
Hamano, Masako
author_facet Yajima, Tomoko
Yoshida, Eriko
Hamano, Masako
author_sort Yajima, Tomoko
collection PubMed
description The cis- and trans-stereoselective radical additions to α-methylene-γ-alkyl- γ-lactams were investigated and the scope and limitation of the reaction were also revealed. This stereoselective radical reaction was used for synthesis of chiral pyroglutamic acid derivatives starting from a commercially available chiral amino acid.
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spelling pubmed-37404932013-08-14 Diastereoselective radical addition to γ-alkyl-α-methylene-γ-butyrolactams and the synthesis of a chiral pyroglutamic acid derivative Yajima, Tomoko Yoshida, Eriko Hamano, Masako Beilstein J Org Chem Full Research Paper The cis- and trans-stereoselective radical additions to α-methylene-γ-alkyl- γ-lactams were investigated and the scope and limitation of the reaction were also revealed. This stereoselective radical reaction was used for synthesis of chiral pyroglutamic acid derivatives starting from a commercially available chiral amino acid. Beilstein-Institut 2013-07-17 /pmc/articles/PMC3740493/ /pubmed/23946839 http://dx.doi.org/10.3762/bjoc.9.161 Text en Copyright © 2013, Yajima et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Yajima, Tomoko
Yoshida, Eriko
Hamano, Masako
Diastereoselective radical addition to γ-alkyl-α-methylene-γ-butyrolactams and the synthesis of a chiral pyroglutamic acid derivative
title Diastereoselective radical addition to γ-alkyl-α-methylene-γ-butyrolactams and the synthesis of a chiral pyroglutamic acid derivative
title_full Diastereoselective radical addition to γ-alkyl-α-methylene-γ-butyrolactams and the synthesis of a chiral pyroglutamic acid derivative
title_fullStr Diastereoselective radical addition to γ-alkyl-α-methylene-γ-butyrolactams and the synthesis of a chiral pyroglutamic acid derivative
title_full_unstemmed Diastereoselective radical addition to γ-alkyl-α-methylene-γ-butyrolactams and the synthesis of a chiral pyroglutamic acid derivative
title_short Diastereoselective radical addition to γ-alkyl-α-methylene-γ-butyrolactams and the synthesis of a chiral pyroglutamic acid derivative
title_sort diastereoselective radical addition to γ-alkyl-α-methylene-γ-butyrolactams and the synthesis of a chiral pyroglutamic acid derivative
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3740493/
https://www.ncbi.nlm.nih.gov/pubmed/23946839
http://dx.doi.org/10.3762/bjoc.9.161
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