{"title":"Synthesis of Optically Active Cyclam and Its Transformations","authors":"Kazuhiro Yoshida, Yuya Miwa, Yakumo Tojima, Miyuki Takahashi, Daichi Shishido","doi":"10.1002/ajoc.202400310","DOIUrl":null,"url":null,"abstract":"<p>Cyclam is a well-known example of a polyaza macrocycle. However, there are few reports of its optically active versions. In this study, we synthesized highly symmetric optically active cyclam (<i>S</i>,<i>S</i>,<i>S</i>,<i>S</i>)-5,7,12,14-tetraphenyl-1,4,8,11-tetraazacyclotetradecane, which has four phenyl groups on the cyclam skeleton, and derivatized it in various ways. We were able to synthesize a chiral Cu complex, an <i>N</i>-ethyl derivative, and a dithiourea from this optically active cyclam. The structures of the chiral Cu complex and dithiourea were verified by single-crystal X-ray diffraction analysis.</p>","PeriodicalId":130,"journal":{"name":"Asian Journal of Organic Chemistry","volume":"13 11","pages":""},"PeriodicalIF":2.8000,"publicationDate":"2024-08-13","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Asian Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/ajoc.202400310","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
Cyclam is a well-known example of a polyaza macrocycle. However, there are few reports of its optically active versions. In this study, we synthesized highly symmetric optically active cyclam (S,S,S,S)-5,7,12,14-tetraphenyl-1,4,8,11-tetraazacyclotetradecane, which has four phenyl groups on the cyclam skeleton, and derivatized it in various ways. We were able to synthesize a chiral Cu complex, an N-ethyl derivative, and a dithiourea from this optically active cyclam. The structures of the chiral Cu complex and dithiourea were verified by single-crystal X-ray diffraction analysis.
Cyclam 是众所周知的多氮杂环大环。然而，有关其光学活性版本的报道却很少。在这项研究中，我们合成了具有高度对称性的光学活性环酰胺 (S,S,S,S,S)-5,7,12,14-四苯基-1,4,8,11-四氮杂环十四烷，其环酰胺骨架上有四个苯基，并通过各种方法对其进行衍生。我们从这种具有光学活性的环戊烷中合成了一种手性 Cu 复合物、一种 N-乙基衍生物和一种二硫脲。单晶 X 射线衍射分析验证了手性铜络合物和二硫脲的结构。
期刊介绍：
Organic chemistry is the fundamental science that stands at the heart of chemistry, biology, and materials science. Research in these areas is vigorous and truly international, with three major regions making almost equal contributions: America, Europe and Asia. Asia now has its own top international organic chemistry journal—the Asian Journal of Organic Chemistry (AsianJOC)
The AsianJOC is designed to be a top-ranked international research journal and publishes primary research as well as critical secondary information from authors across the world. The journal covers organic chemistry in its entirety. Authors and readers come from academia, the chemical industry, and government laboratories.
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