Tetrahedron Letters

Synthesis of β-amino arylketones through the addition of ArLi derivatives to β-aminoesters

PG Lima, LC Sequeira, PRR Costa

Index: Lima, Paulo G.; Sequeira, Lucia C.; Costa, Paulo R.R. Tetrahedron Letters, 2001 , vol. 42, # 21 p. 3525 - 3527

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Citation Number: 19

Abstract

2-Lithiumthiophene and 2-lithiumpyridine were allowed to react with N-substituted β- aminoesters. Only β-amino arylketones were obtained from N-BOC, NH derivatives, while arylenoates were formed (retro-conjugate addition) from those substrates bearing N-Bn, NH 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- ...