Stereoselective Synthesis of Isoquinuclidines through an Aza-[4 + 2] Cycloaddition of Chiral Cyclic 2-Amidodienes

[Image: see text] A highly stereoselective aza-[4 + 2] cycloaddition of chiral cyclic 2-amidodienes with N-sulfonyl aldimines is described. While this Lewis acid promoted heterocycloaddition provides an efficient strategy for constructing optically enriched isoquinuclidines, it is mechanistically in...

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Autores principales: Fang, Li-Chao, Hsung, Richard P.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2014
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3969095/
https://www.ncbi.nlm.nih.gov/pubmed/24621094
http://dx.doi.org/10.1021/ol500390a
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author Fang, Li-Chao
Hsung, Richard P.
author_facet Fang, Li-Chao
Hsung, Richard P.
author_sort Fang, Li-Chao
collection PubMed
description [Image: see text] A highly stereoselective aza-[4 + 2] cycloaddition of chiral cyclic 2-amidodienes with N-sulfonyl aldimines is described. While this Lewis acid promoted heterocycloaddition provides an efficient strategy for constructing optically enriched isoquinuclidines, it is mechanistically intriguing. The cycloaddition favored the endo-II pathway in the absence of a viable bidentate coordination. This represents an unexpected switch from the anticipated endo-I selectivity obtained in the all-carbon cycloaddition.
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spelling pubmed-39690952015-03-12 Stereoselective Synthesis of Isoquinuclidines through an Aza-[4 + 2] Cycloaddition of Chiral Cyclic 2-Amidodienes Fang, Li-Chao Hsung, Richard P. Org Lett [Image: see text] A highly stereoselective aza-[4 + 2] cycloaddition of chiral cyclic 2-amidodienes with N-sulfonyl aldimines is described. While this Lewis acid promoted heterocycloaddition provides an efficient strategy for constructing optically enriched isoquinuclidines, it is mechanistically intriguing. The cycloaddition favored the endo-II pathway in the absence of a viable bidentate coordination. This represents an unexpected switch from the anticipated endo-I selectivity obtained in the all-carbon cycloaddition. American Chemical Society 2014-03-12 2014-03-21 /pmc/articles/PMC3969095/ /pubmed/24621094 http://dx.doi.org/10.1021/ol500390a Text en Copyright © 2014 American Chemical Society
spellingShingle Fang, Li-Chao
Hsung, Richard P.
Stereoselective Synthesis of Isoquinuclidines through an Aza-[4 + 2] Cycloaddition of Chiral Cyclic 2-Amidodienes
title Stereoselective Synthesis of Isoquinuclidines through an Aza-[4 + 2] Cycloaddition of Chiral Cyclic 2-Amidodienes
title_full Stereoselective Synthesis of Isoquinuclidines through an Aza-[4 + 2] Cycloaddition of Chiral Cyclic 2-Amidodienes
title_fullStr Stereoselective Synthesis of Isoquinuclidines through an Aza-[4 + 2] Cycloaddition of Chiral Cyclic 2-Amidodienes
title_full_unstemmed Stereoselective Synthesis of Isoquinuclidines through an Aza-[4 + 2] Cycloaddition of Chiral Cyclic 2-Amidodienes
title_short Stereoselective Synthesis of Isoquinuclidines through an Aza-[4 + 2] Cycloaddition of Chiral Cyclic 2-Amidodienes
title_sort stereoselective synthesis of isoquinuclidines through an aza-[4 + 2] cycloaddition of chiral cyclic 2-amidodienes
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3969095/
https://www.ncbi.nlm.nih.gov/pubmed/24621094
http://dx.doi.org/10.1021/ol500390a
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AT hsungrichardp stereoselectivesynthesisofisoquinuclidinesthroughanaza42cycloadditionofchiralcyclic2amidodienes

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