Nucleophile‐Directed Selective Transformation of cis‐1‐Tosyl‐2‐tosyloxymethyl‐3‐(trifluoromethyl)aziridine into Aziridines,Azetidines, and Benzo‐Fused Dithianes,Oxathianes, Dioxanes,and (Thio)morpholines |
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| Authors: | Sara Kenis Prof?Dr Matthias D'hooghe Prof?Dr Guido Verniest Maaike Reybroeck Tuyet Anh Dang?Thi Chinh Pham?The Tham Thi?Pham Prof?Dr Karl W Törnroos Dr Nguyen Van?Tuyen Prof?Dr Norbert De?Kimpe |
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| Institution: | 1. Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, 9000 Ghent (Belgium), Fax: (+32)?9‐264‐62‐21;2. Current address: Vrije Universiteit Brussel, Faculty of Science and Bio‐engineering Sciences, Department of Chemistry, Pleinlaan 2, 1050 Brussels (Belgium);3. Institute of Chemistry, Vietnam Academy of Sciences and Technology, 18 Hoang Quoc Viet, Cau giay, Hanoi (Vietnam), Fax: (84) 437914648;4. Department of Chemistry, University of Bergen, Allégt 41, 5007 Bergen (Norway) |
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| Abstract: | A five‐step procedure for the synthesis of cis‐1‐tosyl‐2‐tosyloxymethyl‐3‐(trifluoromethyl)aziridine was developed, starting from 1‐ethoxy‐2,2,2‐trifluoroethanol, involving imination, aziridination, ester reduction, hydrogenation, and N‐,O‐ditosylation steps. Further synthetic elaborations revealed a remarkable difference in the reactivity of cis‐1‐tosyl‐2‐tosyloxymethyl‐3‐(trifluoromethyl)aziridine with respect to aromatic sulfur and oxygen nucleophiles, thus enabling the selective deployment of this versatile substrate as a building block for the synthesis of functionalized aziridines, azetidines, and benzo‐fused dithianes, oxathianes, dioxanes, and (thio)morpholines. |
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| Keywords: | aziridines heterocycles oxygen ring expansion sulfur |
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