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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...

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Autores principales: Chen, Chien-Tien, Tsai, Cheng-Che, Tsou, Pei-Kang, Huang, Gou-Tao, Yu, Chin-Hui
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2017
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.
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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
title_full Enantiodivergent Steglich rearrangement of O-carboxylazlactones catalyzed by a chirality switchable helicene containing a 4-aminopyridine unit
title_fullStr Enantiodivergent Steglich rearrangement of O-carboxylazlactones catalyzed by a chirality switchable helicene containing a 4-aminopyridine unit
title_full_unstemmed Enantiodivergent Steglich rearrangement of O-carboxylazlactones catalyzed by a chirality switchable helicene containing a 4-aminopyridine unit
title_short Enantiodivergent Steglich rearrangement of O-carboxylazlactones catalyzed by a chirality switchable helicene containing a 4-aminopyridine unit
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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