Asymmetric Synthesis of Tetrahydroisoquinoline Derivatives through 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines with Allyl Alkyl Ketones

A [3 + 2] 1,3-Dipolar cycloaddition of C,N-cyclic azomethine imines with allyl alkyl ketones has been achieved. The reaction proceeds under mild conditions and tolerates a wide range of functional groups. An array of tetrahydroisoquinoline derivatives is generally constructed with good diastereosele...

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Autores principales: Feng, Guipeng, Ma, Guoyang, Chen, Wenyan, Xu, Shaohong, Wang, Kaikai, Wang, Shaoyan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2021
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8156229/
https://www.ncbi.nlm.nih.gov/pubmed/34067645
http://dx.doi.org/10.3390/molecules26102969
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author Feng, Guipeng
Ma, Guoyang
Chen, Wenyan
Xu, Shaohong
Wang, Kaikai
Wang, Shaoyan
author_facet Feng, Guipeng
Ma, Guoyang
Chen, Wenyan
Xu, Shaohong
Wang, Kaikai
Wang, Shaoyan
author_sort Feng, Guipeng
collection PubMed
description A [3 + 2] 1,3-Dipolar cycloaddition of C,N-cyclic azomethine imines with allyl alkyl ketones has been achieved. The reaction proceeds under mild conditions and tolerates a wide range of functional groups. An array of tetrahydroisoquinoline derivatives is generally constructed with good diastereoselectivities and enantioselectivities (up to >25:1 dr, >95% ee). Moreover, the absolute configuration of the product was previously determined by using the quantum electronic circular dichroism calculation and ECD spectrum method.
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spelling pubmed-81562292021-05-28 Asymmetric Synthesis of Tetrahydroisoquinoline Derivatives through 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines with Allyl Alkyl Ketones Feng, Guipeng Ma, Guoyang Chen, Wenyan Xu, Shaohong Wang, Kaikai Wang, Shaoyan Molecules Article A [3 + 2] 1,3-Dipolar cycloaddition of C,N-cyclic azomethine imines with allyl alkyl ketones has been achieved. The reaction proceeds under mild conditions and tolerates a wide range of functional groups. An array of tetrahydroisoquinoline derivatives is generally constructed with good diastereoselectivities and enantioselectivities (up to >25:1 dr, >95% ee). Moreover, the absolute configuration of the product was previously determined by using the quantum electronic circular dichroism calculation and ECD spectrum method. MDPI 2021-05-17 /pmc/articles/PMC8156229/ /pubmed/34067645 http://dx.doi.org/10.3390/molecules26102969 Text en © 2021 by the authors. https://creativecommons.org/licenses/by/4.0/Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Feng, Guipeng
Ma, Guoyang
Chen, Wenyan
Xu, Shaohong
Wang, Kaikai
Wang, Shaoyan
Asymmetric Synthesis of Tetrahydroisoquinoline Derivatives through 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines with Allyl Alkyl Ketones
title Asymmetric Synthesis of Tetrahydroisoquinoline Derivatives through 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines with Allyl Alkyl Ketones
title_full Asymmetric Synthesis of Tetrahydroisoquinoline Derivatives through 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines with Allyl Alkyl Ketones
title_fullStr Asymmetric Synthesis of Tetrahydroisoquinoline Derivatives through 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines with Allyl Alkyl Ketones
title_full_unstemmed Asymmetric Synthesis of Tetrahydroisoquinoline Derivatives through 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines with Allyl Alkyl Ketones
title_short Asymmetric Synthesis of Tetrahydroisoquinoline Derivatives through 1,3-Dipolar Cycloaddition of C,N-Cyclic Azomethine Imines with Allyl Alkyl Ketones
title_sort asymmetric synthesis of tetrahydroisoquinoline derivatives through 1,3-dipolar cycloaddition of c,n-cyclic azomethine imines with allyl alkyl ketones
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8156229/
https://www.ncbi.nlm.nih.gov/pubmed/34067645
http://dx.doi.org/10.3390/molecules26102969
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