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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Bibliographic Details
Published inTetrahedron letters Vol. 42; no. 21; pp. 3525 - 3527
Main Authors Lima, PG, Sequeira, LC, Costa, PRR
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 21.05.2001
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
METHOXY-N-METHYLAMIDES
KETONES
ACIDS
CONVERSION
ESTERS
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Summary: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.
ISSN:0040-4039
DOI:10.1016/S0040-4039(01)00358-6