Catalytic asymmetric synthesis of stable oxetenes via Lewis acid-promoted [2+2] cycloaddition |
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Authors: | Aikawa Kohsuke Hioki Yūta Shimizu Natsumi Mikami Koichi |
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Institution: | Department of Applied Chemistry, Tokyo Institute of Technology, Tokyo 152-8552, Japan. |
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Abstract: | A highly enantioselective and atom-economical 2 + 2] cycloaddition of various alkynes with trifluoropyruvate using a dicationic (S)-BINAP-Pd catalyst has been established. This is the first enantioselective synthesis of stable oxetene derivatives, whose structure has been clarified by X-ray analysis. This catalytic process offers a practical synthetic method for oxetene derivatives (catalyst loading: up to 0.1 mol %), which can serve as novel chiral building blocks for pharmaceuticals and agrochemicals and can also be transformed into a variety of enantiomerically enriched CF(3)-substituted compounds with high stereoselectivity. |
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