Epoxide-Mediated Stevens Rearrangements of α-Amino-Acid-Derived Tertiary Allylic,Propargylic, and Benzylic Amines: Convenient Access to Polysubstituted Morpholin-2-ones |
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| Authors: | You-Xiang Jin Bang-Kui Yu Si-Ping Qin Prof Dr Shi-Kai Tian |
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| Institution: | 1. Hefei National Laboratory for Physical Sciences at the Microscale, Center for Excellence in Molecular Synthesis, and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026 China
These authors contributed equally to this work.;2. Hefei National Laboratory for Physical Sciences at the Microscale, Center for Excellence in Molecular Synthesis, and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui, 230026 China |
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| Abstract: | A new strategy has been established for the synthesis of polysubstituted morpholin-2-ones through Stevens rearrangements of tertiary amines via in situ activation with epoxides. A range of α-amino acid-derived tertiary allylic, propargylic, and benzylic amines reacted with epoxides in the presence of zinc halide catalysts to afford structurally diverse allyl-, allenyl-, and benzyl-substituted morpholin-2-ones, respectively, in moderate-to-good yields with high regioselectivity. The process involves 2,3]- and 1,2]-Stevens rearrangements of quaternary ammonium ylide intermediates and constitutes a very convenient method to prepare polysubstituted morpholin-2-ones through tandem formation of C−N, C−O, and C−C bonds. Moreover, replacing epoxides with aziridines permitted the synthesis of polysubstituted piperazin-2-ones. |
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| Keywords: | amines ammonium ylides epoxides morpholin-2-ones Stevens rearrangement |
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