Generation and Electrophile Trapping of N-Boc-2-lithio-2-azetine: Synthesis of 2-Substituted 2-Azetines

[Image: see text] s-BuLi-induced α-lithiation–elimination of LiOMe from N-Boc-3-methoxyazetidine and further in situ α-lithiation generates N-Boc-2-lithio-2-azetine which can be trapped with electrophiles, either directly (carbonyl or heteroatom electrophiles) or after transmetalation to copper (all...

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Autores principales: Hodgson, David M., Pearson, Christopher I., Kazmi, Madiha
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3929120/
https://www.ncbi.nlm.nih.gov/pubmed/24410016
http://dx.doi.org/10.1021/ol403626k
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author Hodgson, David M.
Pearson, Christopher I.
Kazmi, Madiha
author_facet Hodgson, David M.
Pearson, Christopher I.
Kazmi, Madiha
author_sort Hodgson, David M.
collection PubMed
description [Image: see text] s-BuLi-induced α-lithiation–elimination of LiOMe from N-Boc-3-methoxyazetidine and further in situ α-lithiation generates N-Boc-2-lithio-2-azetine which can be trapped with electrophiles, either directly (carbonyl or heteroatom electrophiles) or after transmetalation to copper (allowing allylations and propargylations), providing a concise access to 2-substituted 2-azetines.
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spelling pubmed-39291202014-02-20 Generation and Electrophile Trapping of N-Boc-2-lithio-2-azetine: Synthesis of 2-Substituted 2-Azetines Hodgson, David M. Pearson, Christopher I. Kazmi, Madiha Org Lett [Image: see text] s-BuLi-induced α-lithiation–elimination of LiOMe from N-Boc-3-methoxyazetidine and further in situ α-lithiation generates N-Boc-2-lithio-2-azetine which can be trapped with electrophiles, either directly (carbonyl or heteroatom electrophiles) or after transmetalation to copper (allowing allylations and propargylations), providing a concise access to 2-substituted 2-azetines. American Chemical Society 2014-01-10 2014-02-07 /pmc/articles/PMC3929120/ /pubmed/24410016 http://dx.doi.org/10.1021/ol403626k Text en Copyright © 2014 American Chemical Society Terms of Use CC-BY (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html)
spellingShingle Hodgson, David M.
Pearson, Christopher I.
Kazmi, Madiha
Generation and Electrophile Trapping of N-Boc-2-lithio-2-azetine: Synthesis of 2-Substituted 2-Azetines
title Generation and Electrophile Trapping of N-Boc-2-lithio-2-azetine: Synthesis of 2-Substituted 2-Azetines
title_full Generation and Electrophile Trapping of N-Boc-2-lithio-2-azetine: Synthesis of 2-Substituted 2-Azetines
title_fullStr Generation and Electrophile Trapping of N-Boc-2-lithio-2-azetine: Synthesis of 2-Substituted 2-Azetines
title_full_unstemmed Generation and Electrophile Trapping of N-Boc-2-lithio-2-azetine: Synthesis of 2-Substituted 2-Azetines
title_short Generation and Electrophile Trapping of N-Boc-2-lithio-2-azetine: Synthesis of 2-Substituted 2-Azetines
title_sort generation and electrophile trapping of n-boc-2-lithio-2-azetine: synthesis of 2-substituted 2-azetines
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3929120/
https://www.ncbi.nlm.nih.gov/pubmed/24410016
http://dx.doi.org/10.1021/ol403626k
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