Synthesis of beta-amino arylketones through the addition of ArLi derivatives to beta-aminoesters
2-Lithiumthiophene and 2-lithiumpyridine were allowed to react with iv-substituted beta -aminoesters. Only beta -amino arylketones were obtained from N-BOC, IV-H derivatives, while arylenoates were formed (retro-conjugate addition) from those substrates bearing N-Bn, N-H substituents, despite the ar...
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| Published in | Tetrahedron letters Vol. 42; no. 21; pp. 3525 - 3527 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
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| Abstract | 2-Lithiumthiophene and 2-lithiumpyridine were allowed to react with iv-substituted beta -aminoesters. Only beta -amino arylketones were obtained from N-BOC, IV-H derivatives, while arylenoates were formed (retro-conjugate addition) from those substrates bearing N-Bn, N-H substituents, despite the aryllithium used. When the nitrogen is disubstituted (BOC and Bn), the product distribution depended on the nucleophile, leading to tertiary alcohols for 2-lithiumthiophene or ketones for 2-lithiumpyridine. Tertiary alcohols were also formed when PhLi was used as a nucleophile. (C) 2001 Elsevier Science Ltd. All rights reserved. |
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| AbstractList | 2-Lithiumthiophene and 2-lithiumpyridine were allowed to react with iv-substituted beta -aminoesters. Only beta -amino arylketones were obtained from N-BOC, IV-H derivatives, while arylenoates were formed (retro-conjugate addition) from those substrates bearing N-Bn, N-H substituents, despite the aryllithium used. When the nitrogen is disubstituted (BOC and Bn), the product distribution depended on the nucleophile, leading to tertiary alcohols for 2-lithiumthiophene or ketones for 2-lithiumpyridine. Tertiary alcohols were also formed when PhLi was used as a nucleophile. (C) 2001 Elsevier Science Ltd. All rights reserved. |
| Author | Costa, PRR Sequeira, LC Lima, PG |
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| Cites_doi | 10.1016/0040-4039(93)88086-X 10.1016/0040-4039(96)00518-7 10.1021/jo00157a038 10.1016/0040-4039(96)00557-6 10.1021/jo00261a036 10.1021/jo951754c 10.1016/0040-4039(95)02053-5 10.1021/jo970277q 10.1016/S0040-4039(01)91316-4 10.1016/S0040-4020(97)10399-4 10.1021/jo00388a025 10.1016/S0040-4039(01)80629-8 10.1021/jo00007a043 10.1016/S0040-4039(00)88082-X 10.1055/s-1998-1831 |
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| Title | Synthesis of beta-amino arylketones through the addition of ArLi derivatives to beta-aminoesters |
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