Enantioselective phase-transfer catalyzed alkylation of 1-methyl-7-methoxy-2-tetralone: an effective route to dezocine

In order to prepare asymmetrically (R)-(+)-1-(5-bromopentyl)-1-methyl-7-methoxy-2-tetralone (3a), a key intermediate of dezocine, 17 cinchona alkaloid-derived catalysts were prepared and screened for the enantioselective alkylation of 1-methyl-7-methoxy-2-tetralone with 1,5-dibromopentane, and the b...

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Autores principales: Li, Ruipeng, Liu, Zhenren, Chen, Liang, Pan, Jing, Zhou, Weicheng
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2018
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6009193/
https://www.ncbi.nlm.nih.gov/pubmed/29977405
http://dx.doi.org/10.3762/bjoc.14.119
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author Li, Ruipeng
Liu, Zhenren
Chen, Liang
Pan, Jing
Zhou, Weicheng
author_facet Li, Ruipeng
Liu, Zhenren
Chen, Liang
Pan, Jing
Zhou, Weicheng
author_sort Li, Ruipeng
collection PubMed
description In order to prepare asymmetrically (R)-(+)-1-(5-bromopentyl)-1-methyl-7-methoxy-2-tetralone (3a), a key intermediate of dezocine, 17 cinchona alkaloid-derived catalysts were prepared and screened for the enantioselective alkylation of 1-methyl-7-methoxy-2-tetralone with 1,5-dibromopentane, and the best catalyst (C7) was identified. In addition, optimizations of the alkylation were carried out so that the process became practical and effective.
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spelling pubmed-60091932018-07-05 Enantioselective phase-transfer catalyzed alkylation of 1-methyl-7-methoxy-2-tetralone: an effective route to dezocine Li, Ruipeng Liu, Zhenren Chen, Liang Pan, Jing Zhou, Weicheng Beilstein J Org Chem Full Research Paper In order to prepare asymmetrically (R)-(+)-1-(5-bromopentyl)-1-methyl-7-methoxy-2-tetralone (3a), a key intermediate of dezocine, 17 cinchona alkaloid-derived catalysts were prepared and screened for the enantioselective alkylation of 1-methyl-7-methoxy-2-tetralone with 1,5-dibromopentane, and the best catalyst (C7) was identified. In addition, optimizations of the alkylation were carried out so that the process became practical and effective. Beilstein-Institut 2018-06-11 /pmc/articles/PMC6009193/ /pubmed/29977405 http://dx.doi.org/10.3762/bjoc.14.119 Text en Copyright © 2018, Li et al. https://creativecommons.org/licenses/by/4.0https://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/4.0), 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
Li, Ruipeng
Liu, Zhenren
Chen, Liang
Pan, Jing
Zhou, Weicheng
Enantioselective phase-transfer catalyzed alkylation of 1-methyl-7-methoxy-2-tetralone: an effective route to dezocine
title Enantioselective phase-transfer catalyzed alkylation of 1-methyl-7-methoxy-2-tetralone: an effective route to dezocine
title_full Enantioselective phase-transfer catalyzed alkylation of 1-methyl-7-methoxy-2-tetralone: an effective route to dezocine
title_fullStr Enantioselective phase-transfer catalyzed alkylation of 1-methyl-7-methoxy-2-tetralone: an effective route to dezocine
title_full_unstemmed Enantioselective phase-transfer catalyzed alkylation of 1-methyl-7-methoxy-2-tetralone: an effective route to dezocine
title_short Enantioselective phase-transfer catalyzed alkylation of 1-methyl-7-methoxy-2-tetralone: an effective route to dezocine
title_sort enantioselective phase-transfer catalyzed alkylation of 1-methyl-7-methoxy-2-tetralone: an effective route to dezocine
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6009193/
https://www.ncbi.nlm.nih.gov/pubmed/29977405
http://dx.doi.org/10.3762/bjoc.14.119
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