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Enantiodivergent Steglich rearrangement of O-carboxylazlactones catalyzed by a chirality switchable helicene containing a 4-aminopyridine unit
A pseudo-enantiomeric pair of optically switchable helicenes containing a catalytic 4-N-methylaminopyridine (MAP) bottom unit and a C (2)-symmetric, (10R,11R)-dimethoxymethyl-dibenzosuberane top template was synthesized. They underwent complementary photoswitching at 290 nm (P/M′, <1/>99) and...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
Royal Society of Chemistry
2017
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5341298/ https://www.ncbi.nlm.nih.gov/pubmed/28451199 http://dx.doi.org/10.1039/c6sc02646j |
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author | Chen, Chien-Tien Tsai, Cheng-Che Tsou, Pei-Kang Huang, Gou-Tao Yu, Chin-Hui |
author_facet | Chen, Chien-Tien Tsai, Cheng-Che Tsou, Pei-Kang Huang, Gou-Tao Yu, Chin-Hui |
author_sort | Chen, Chien-Tien |
collection | PubMed |
description | A pseudo-enantiomeric pair of optically switchable helicenes containing a catalytic 4-N-methylaminopyridine (MAP) bottom unit and a C (2)-symmetric, (10R,11R)-dimethoxymethyl-dibenzosuberane top template was synthesized. They underwent complementary photoswitching at 290 nm (P/M′, <1/>99) and 340 nm (P/M′, 91/9) and unidirectional thermo-rotation at 130 °C (P/M′, >99/<1). They were utilized to catalyze enantiodivergent Steglich rearrangement of O- to C-carboxylazlactones, with formation of either enantiomer with up to 91% ee (R) and 94% ee (S), respectively. |
format | Online Article Text |
id | pubmed-5341298 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2017 |
publisher | Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
spelling | pubmed-53412982017-04-27 Enantiodivergent Steglich rearrangement of O-carboxylazlactones catalyzed by a chirality switchable helicene containing a 4-aminopyridine unit Chen, Chien-Tien Tsai, Cheng-Che Tsou, Pei-Kang Huang, Gou-Tao Yu, Chin-Hui Chem Sci Chemistry A pseudo-enantiomeric pair of optically switchable helicenes containing a catalytic 4-N-methylaminopyridine (MAP) bottom unit and a C (2)-symmetric, (10R,11R)-dimethoxymethyl-dibenzosuberane top template was synthesized. They underwent complementary photoswitching at 290 nm (P/M′, <1/>99) and 340 nm (P/M′, 91/9) and unidirectional thermo-rotation at 130 °C (P/M′, >99/<1). They were utilized to catalyze enantiodivergent Steglich rearrangement of O- to C-carboxylazlactones, with formation of either enantiomer with up to 91% ee (R) and 94% ee (S), respectively. Royal Society of Chemistry 2017-01-01 2016-08-25 /pmc/articles/PMC5341298/ /pubmed/28451199 http://dx.doi.org/10.1039/c6sc02646j Text en This journal is © The Royal Society of Chemistry 2016 http://creativecommons.org/licenses/by-nc/3.0/ This is an Open Access article distributed under the terms of the Creative Commons Attribution-NonCommercial 3.0 Unported License (http://creativecommons.org/licenses/by-nc/3.0/) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited. |
spellingShingle | Chemistry Chen, Chien-Tien Tsai, Cheng-Che Tsou, Pei-Kang Huang, Gou-Tao Yu, Chin-Hui Enantiodivergent Steglich rearrangement of O-carboxylazlactones catalyzed by a chirality switchable helicene containing a 4-aminopyridine unit |
title | Enantiodivergent Steglich rearrangement of O-carboxylazlactones catalyzed by a chirality switchable helicene containing a 4-aminopyridine unit
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title_full | Enantiodivergent Steglich rearrangement of O-carboxylazlactones catalyzed by a chirality switchable helicene containing a 4-aminopyridine unit
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title_fullStr | Enantiodivergent Steglich rearrangement of O-carboxylazlactones catalyzed by a chirality switchable helicene containing a 4-aminopyridine unit
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title_full_unstemmed | Enantiodivergent Steglich rearrangement of O-carboxylazlactones catalyzed by a chirality switchable helicene containing a 4-aminopyridine unit
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title_short | Enantiodivergent Steglich rearrangement of O-carboxylazlactones catalyzed by a chirality switchable helicene containing a 4-aminopyridine unit
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title_sort | enantiodivergent steglich rearrangement of o-carboxylazlactones catalyzed by a chirality switchable helicene containing a 4-aminopyridine unit |
topic | Chemistry |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5341298/ https://www.ncbi.nlm.nih.gov/pubmed/28451199 http://dx.doi.org/10.1039/c6sc02646j |
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