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    Home > Zhou Haifeng group of Three Gorges University: synthesis of chiral alcohols by alkyne hydration asymmetric hydrogenation in series under simple conditions

    Zhou Haifeng group of Three Gorges University: synthesis of chiral alcohols by alkyne hydration asymmetric hydrogenation in series under simple conditions

    • Last Update: 2018-02-07
    • Source: Internet
    • Author: User
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    In January, Zhou Haifeng group of Three Gorges University was invited to be our first reporting object (click to check) Recently, Zhou Haifeng group has made some new progress in the synthesis of chiral alcohols In this regard, CBG information first paid attention to and reported the latest research results of "old friends" Leading scientific achievements: the conversion of alkyne to chiral alkyne by hydration asymmetric hydrogenation in series reaction under simple conditions has been widely concerned in organic synthesis, but the direct conversion of alkyne to chiral alcohol by one pot method has certain challenges In this study, a new method for the direct conversion of alkynes into chiral alcohols by the series asymmetric hydrogenation catalyzed by trifluoromethane sulfonic acid and chiral metal ruthenium complex under simple conditions was reported, which solved the key problems of the harmonious coexistence and synergistic catalysis of catalysts in the two-step one pot reaction, and obtained a series of chiral alcohols, all of which have extensive functional group tolerance, The direct conversion of aryl diyne or triyne to chiral diol or triol was realized for the first time This method has the advantages of step economy, atom economy and one pot method Figure 1 Conversion of alkyne to alcohol (source: org Lett.) the author first optimized the conditions for the first step of hydration reaction, and then screened the catalyst, alkali, hydrogen pressure and temperature for the second step of asymmetric hydrogenation The optimal reaction conditions were determined as follows: alkyne (0.5 mmol), tfoh (20 mol%), H 2O (2 equiv), CF 3CH 2OH (2 ml), 40 Step 2: (s, s) - 1C (5 mol%), Koh (0.25equiv), H 2 (20 ATM), 40 ℃, 24 h (Table 1) Table 1 Determination of the optimal reaction conditions (source: org Lett.) after obtaining the optimal reaction conditions, the research team expanded the substrate to obtain a series of chiral alcohols For the terminal arylacetylene, whether it is the phenylacetylene (2b-2m) with electron absorption group or electron donor group, it can be converted into corresponding chiral alcohol (3b-3m), with EE value of 81-99% The first hydration of the electron deficient arylacetylene requires higher reaction temperature and longer reaction time In addition, non terminal aryl alkynes (2n - 2R) can also be successfully converted into corresponding chiral alcohols, with a yield of 72-83% and an EE value of 93-99% Table 2 Substrate development (source: org Lett.) interestingly, the direct conversion of aryl diyne or triyne to chiral diol or triol has been realized for the first time in this study, with high yield, enantioselectivity and non enantioselectivity (Table 3) Table 3 The direct conversion of aryl diyne or triyne to chiral diol or triol (source: org Lett.) finally, the gram scale synthesis of phenylacetylene to (s) - 1-phenylethanol was successfully realized with a yield of 92% and an EE value of 99% (Table 4) Table 4 Gram level synthesis of (s) - 1-phenylethanol (source: org Lett.) this achievement was recently published in organic letter (DOI: 10.1021 / ACS Orglett 8b00034) Liu sensheng, a postgraduate, is the first author, Zhou Haifeng, Ph.D is the corresponding author, and the partners include Dr Liu Qixing, Liu Huan, a postgraduate, and LV Jinliang, R & D Department of Yichang humanwell Pharmaceutical Co., Ltd The research was supported by the National Natural Science Foundation of China (21202092), the research project of Three Gorges University (kj2012b080, kj2014h008), the excellent master's thesis training fund of Three Gorges University (2017ypy083) and the Yichang humanwell cooperation project (sdhz2015003) Liu sensheng, the first author, graduated from the school of biology and pharmacy of Three Gorges University with a Bachelor of Science Degree in chemical biology in June 2015 Zhou Haifeng is a postgraduate student in the research group of Three Gorges University His research direction is organic synthesis methodology His research interest is catalytic asymmetric synthesis and asymmetric series reaction He plans to go to Max Planck Institute in Germany to study for Ph.D As the first author, he has published 3 research papers in org Lett., org Chem Front., chin J org Chem., applied for 4 invention patents and authorized 1 Paper link: http://pubs.acs.org/doi/10.1021/acs.orglett.8b00034 about people and research from now on, CBG information decided to change the name of "CBG people" channel to "people and research" channel After the name change, we will continue to pay attention to and follow up the scientific research activities and achievements of researchers, and report them in a richer form Today, science and technology elements are increasingly valued in economic life, China has ushered in the "node of science and technology explosion" Behind the progress of science and technology is the work of countless scientists In the field of chemistry, in the context of the pursuit of innovation driven, international cooperation has been strengthened, the influence of Returned Scholars in the field of R & D has become increasingly prominent, and many excellent research groups have emerged in China For this reason, CBG information adopts the 1 + X reporting mechanism CBG information, chembeango app, chembeango official microblog, CBG wechat subscription number and other platforms jointly launch the column of "people and scientific research", approach the representative research groups in China, pay attention to their research, listen to their stories, record their demeanor, and explore their scientific research spirit
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