Synthesis of Three‐, Five‐, and Six‐Membered Heterocycles Derived from New β‐Amino‐α‐(trifluoromethyl) Alcohols |
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| Authors: | Grzegorz Mlostoń Anthony Linden Heinz Heimgartner |
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| Affiliation: | 1. University of ?ód?, Department of Organic and Applied Chemistry, Tamka 12, PL‐91‐403 ?ód?, (phone: +48?42?635?5761;2. fax: +48?42?665?5162);3. Organisch‐chemisches Institut der Universit?t Zürich, Winterthurerstrasse 190, CH‐8057 Zürich, (phone: +41?44?635?4282;4. fax: +41?44?635?6812) |
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| Abstract: | Nucleophilic trifluoromethylation of α‐imino ketones 2 , derived from arylglyoxal, with Ruppert–Prakash reagent (CF3SiMe3) offers a convenient access to the corresponding O‐silylated β‐imino‐α‐(trifluoromethyl) alcohols. In a ‘one‐pot’ procedure, by treatment with NaBH4, these products smoothly undergo reduction and desilylation yielding the expected β‐amino‐α‐(trifluoromethyl) alcohols 4 . The latter were used as starting materials for the synthesis of diverse trifluoromethylated heterocycles, including aziridines 5 , 1,3‐oxazolidines 8 , 1,3‐oxazolidin‐2‐ones 9 , 1,3,2‐oxazaphospholidine 2‐oxides 10 , 1,2,3‐oxathiazolidine 2‐oxides 11 , and morpholine‐2,3‐diones 12 . An optically active 5‐(trifluoromethyl)‐substituted 1,3‐oxazolidin‐2‐one 9g was also obtained. |
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| Keywords: | Alcohols, β ‐amino‐α ‐(trifluoromethyl) Aziridines, 2‐(trifluoromethyl)‐ 1,3‐Oxazolidines, 5‐(trifluoromethyl)‐ 1,3,2‐Oxazaphospholidines, 5‐(trifluoromethyl)‐ 1,2,3‐Oxathiazolidines, 5‐(trifluoromethyl)‐ Trifluoromethyl heterocycles X‐Ray crystallography |
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