Acid-free,organocatalytic acetalization |
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| Institution: | 1. Department of Chemistry, Indian Institute of Science Education and Research Berhampur, Government ITI, Engineering School Junction, Berhampur, Odisha 760 010, India;2. Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur 208 016, Uttar Pradesh, India;3. Department of Chemistry, Indian Institute of Science Education and Research Bhopal, Bhopal Bypass Road, Bhauri, Bhopal 462 066, Madhya Pradesh, India;1. The Institute of Scientific and Industrial Research, Osaka University, Ibaraki, Osaka 567-0047, Japan;2. Compound Library Screening Center, Graduate School of Pharmaceutical Sciences, Osaka University, Yamadaoka, Suita, Osaka 565-0871, Japan;3. Cancer Center, Faculty of Medicine, Shimane University, Izumo 693-8501, Japan;1. Generic Drug Research Center of Guizhou Province, Green Pharmaceuticals Engineering Research Center of Guizhou Province, School of Pharmacy, Zunyi Medical University, Zunyi, 563000, PR China;2. National Engineering Research Center of Chiral Drugs, Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu, 610041, PR China |
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| Abstract: | The acid-free, organocatalytic acetalization of various aldehydes and ketones with N,N′-bis3,5-bis(trifluoromethyl)phenyl]thiourea is presented. The neutral, double hydrogen bonding thiourea catalyst can be used at very low loadings of 0.01–1 mol% at room temperature to furnish the respective acetals in 65–99% yield at turnover frequencies around 600 h−1. Acid-labile TBDMS-protected as well as unsaturated aldehydes can be converted efficiently into their acetals utilizing this very mild and highly practical method. |
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