A general, enantioselective synthesis of N-alkyl terminal aziridines and C2-functionalized azetidines via organocatalysis

A short, high-yielding protocol involving the enantioselective α-chlorination of aldehydes has been developed for the enantioselective synthesis of C2-functionalized aziridines and N-alkyl terminal azetidines from a common intermediate. This methodology allows for the rapid preparation of functional...

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Autores principales: Senter, Timothy J., O’Reilly, Matthew C., Chong, Katherine M., Sulikowski, Gary A., Lindsley, Craig W.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: 2015
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4730893/
https://www.ncbi.nlm.nih.gov/pubmed/26834294
http://dx.doi.org/10.1016/j.tetlet.2015.01.140
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author Senter, Timothy J.
O’Reilly, Matthew C.
Chong, Katherine M.
Sulikowski, Gary A.
Lindsley, Craig W.
author_facet Senter, Timothy J.
O’Reilly, Matthew C.
Chong, Katherine M.
Sulikowski, Gary A.
Lindsley, Craig W.
author_sort Senter, Timothy J.
collection PubMed
description A short, high-yielding protocol involving the enantioselective α-chlorination of aldehydes has been developed for the enantioselective synthesis of C2-functionalized aziridines and N-alkyl terminal azetidines from a common intermediate. This methodology allows for the rapid preparation of functionalized aziridines in 50–73% overall yields and 88–94% ee, and azetidines in 22–32% overall yields and 84–92% ee. Moreover, we developed a scalable and cost-effective route to the key organocatalyst (54% overall yield, >95% dr).
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spelling pubmed-47308932016-03-04 A general, enantioselective synthesis of N-alkyl terminal aziridines and C2-functionalized azetidines via organocatalysis Senter, Timothy J. O’Reilly, Matthew C. Chong, Katherine M. Sulikowski, Gary A. Lindsley, Craig W. Tetrahedron Lett Article A short, high-yielding protocol involving the enantioselective α-chlorination of aldehydes has been developed for the enantioselective synthesis of C2-functionalized aziridines and N-alkyl terminal azetidines from a common intermediate. This methodology allows for the rapid preparation of functionalized aziridines in 50–73% overall yields and 88–94% ee, and azetidines in 22–32% overall yields and 84–92% ee. Moreover, we developed a scalable and cost-effective route to the key organocatalyst (54% overall yield, >95% dr). 2015-03-04 /pmc/articles/PMC4730893/ /pubmed/26834294 http://dx.doi.org/10.1016/j.tetlet.2015.01.140 Text en http://creativecommons.org/licenses/by-nc-nd/4.0/ This manuscript version is made available under the CC BY-NC-ND 4.0 license
spellingShingle Article
Senter, Timothy J.
O’Reilly, Matthew C.
Chong, Katherine M.
Sulikowski, Gary A.
Lindsley, Craig W.
A general, enantioselective synthesis of N-alkyl terminal aziridines and C2-functionalized azetidines via organocatalysis
title A general, enantioselective synthesis of N-alkyl terminal aziridines and C2-functionalized azetidines via organocatalysis
title_full A general, enantioselective synthesis of N-alkyl terminal aziridines and C2-functionalized azetidines via organocatalysis
title_fullStr A general, enantioselective synthesis of N-alkyl terminal aziridines and C2-functionalized azetidines via organocatalysis
title_full_unstemmed A general, enantioselective synthesis of N-alkyl terminal aziridines and C2-functionalized azetidines via organocatalysis
title_short A general, enantioselective synthesis of N-alkyl terminal aziridines and C2-functionalized azetidines via organocatalysis
title_sort general, enantioselective synthesis of n-alkyl terminal aziridines and c2-functionalized azetidines via organocatalysis
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4730893/
https://www.ncbi.nlm.nih.gov/pubmed/26834294
http://dx.doi.org/10.1016/j.tetlet.2015.01.140
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