{"title":"基于dabco的离子盐:合成、表征及在不对称还原反应中作为有机催化剂的应用","authors":"PAWANPREET KAUR, MEGHA T KURIAKOSE, ASWARE ARATI DATTATRAY, NANCY, HARISH KUMAR CHOPRA","doi":"10.1007/s12039-023-02199-6","DOIUrl":null,"url":null,"abstract":"<div><p>GUMBOS (group of uniform materials based on organic salts) are highly functional and tunable organic ionic materials that exhibit a solid state at room temperature, composed of oppositely charged bulky ions with high thermal stability. A variety of GUMBOS has been designed and synthesized by selecting appropriate ion pairs to use in targeted applications of different fields. Herein, parent DABCO-based GUMBOS were synthesized from the reaction of terpene such as (-)-menthol or (-)-borneol or (+)-fenchol and chloroacetic acid followed by DABCO. To formulate GUMBOS derivatives, the parent salt (with chloride counter-anion) was modified through an anion exchange metathesis process by taking different sodium/potassium salts. Structure elucidation was done through NMR, polarimeter, TGA, and GC-MS techniques. The synthesized ionic species were employed as organocatalysts in the enantioselective reduction reactions of various prochiral ketones to chiral alcohols. Low to good enantiomeric excess was obtained.</p><h3>Graphical Abstract</h3><p>The easily available and low-cost parent compounds <i>i.e.,</i> terpenes and DABCO were used for the synthesis of GUMBOS through facile and simple synthetic routes. The salts were obtained with good yield, possessed optical activity, and had high thermal stability. Further, the organocatalytic role of salts was studied in asymmetric reduction reactions.\n</p><div><figure><div><div><picture><img></picture></div></div></figure></div></div>","PeriodicalId":616,"journal":{"name":"Journal of Chemical Sciences","volume":null,"pages":null},"PeriodicalIF":1.7000,"publicationDate":"2023-07-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://link.springer.com/content/pdf/10.1007/s12039-023-02199-6.pdf","citationCount":"0","resultStr":"{\"title\":\"DABCO-based ionic salts: synthesis, characterization, and application as organocatalysts in asymmetric reduction reactions\",\"authors\":\"PAWANPREET KAUR, MEGHA T KURIAKOSE, ASWARE ARATI DATTATRAY, NANCY, HARISH KUMAR CHOPRA\",\"doi\":\"10.1007/s12039-023-02199-6\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>GUMBOS (group of uniform materials based on organic salts) are highly functional and tunable organic ionic materials that exhibit a solid state at room temperature, composed of oppositely charged bulky ions with high thermal stability. A variety of GUMBOS has been designed and synthesized by selecting appropriate ion pairs to use in targeted applications of different fields. Herein, parent DABCO-based GUMBOS were synthesized from the reaction of terpene such as (-)-menthol or (-)-borneol or (+)-fenchol and chloroacetic acid followed by DABCO. To formulate GUMBOS derivatives, the parent salt (with chloride counter-anion) was modified through an anion exchange metathesis process by taking different sodium/potassium salts. Structure elucidation was done through NMR, polarimeter, TGA, and GC-MS techniques. The synthesized ionic species were employed as organocatalysts in the enantioselective reduction reactions of various prochiral ketones to chiral alcohols. Low to good enantiomeric excess was obtained.</p><h3>Graphical Abstract</h3><p>The easily available and low-cost parent compounds <i>i.e.,</i> terpenes and DABCO were used for the synthesis of GUMBOS through facile and simple synthetic routes. The salts were obtained with good yield, possessed optical activity, and had high thermal stability. Further, the organocatalytic role of salts was studied in asymmetric reduction reactions.\\n</p><div><figure><div><div><picture><img></picture></div></div></figure></div></div>\",\"PeriodicalId\":616,\"journal\":{\"name\":\"Journal of Chemical Sciences\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.7000,\"publicationDate\":\"2023-07-28\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://link.springer.com/content/pdf/10.1007/s12039-023-02199-6.pdf\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Chemical Sciences\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s12039-023-02199-6\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Chemical Sciences","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s12039-023-02199-6","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
DABCO-based ionic salts: synthesis, characterization, and application as organocatalysts in asymmetric reduction reactions
GUMBOS (group of uniform materials based on organic salts) are highly functional and tunable organic ionic materials that exhibit a solid state at room temperature, composed of oppositely charged bulky ions with high thermal stability. A variety of GUMBOS has been designed and synthesized by selecting appropriate ion pairs to use in targeted applications of different fields. Herein, parent DABCO-based GUMBOS were synthesized from the reaction of terpene such as (-)-menthol or (-)-borneol or (+)-fenchol and chloroacetic acid followed by DABCO. To formulate GUMBOS derivatives, the parent salt (with chloride counter-anion) was modified through an anion exchange metathesis process by taking different sodium/potassium salts. Structure elucidation was done through NMR, polarimeter, TGA, and GC-MS techniques. The synthesized ionic species were employed as organocatalysts in the enantioselective reduction reactions of various prochiral ketones to chiral alcohols. Low to good enantiomeric excess was obtained.
Graphical Abstract
The easily available and low-cost parent compounds i.e., terpenes and DABCO were used for the synthesis of GUMBOS through facile and simple synthetic routes. The salts were obtained with good yield, possessed optical activity, and had high thermal stability. Further, the organocatalytic role of salts was studied in asymmetric reduction reactions.
期刊介绍:
Journal of Chemical Sciences is a monthly journal published by the Indian Academy of Sciences. It formed part of the original Proceedings of the Indian Academy of Sciences – Part A, started by the Nobel Laureate Prof C V Raman in 1934, that was split in 1978 into three separate journals. It was renamed as Journal of Chemical Sciences in 2004. The journal publishes original research articles and rapid communications, covering all areas of chemical sciences. A significant feature of the journal is its special issues, brought out from time to time, devoted to conference symposia/proceedings in frontier areas of the subject, held not only in India but also in other countries.