Reação entre fenilnitrometanos e enoato derivado do D-manitol na presença de TBAF ou DBU: adição conjugada sin-seletiva e reação de NEF consecutiva

Química Nova

Ayres G. Dias²  Vagner D. Pinho¹  Paulo R. R. Costa¹ 

[1] ,Universidade do Estado do Rio de Janeiro Instituto de Química Rio de Janeiro RJ ,Brasil

关键词: Nef reaction;    chiral enoates;    stereoselective conjugate addition;   

DOI  :  10.1590/S0100-40422008000400024

来源: SciELO

【 摘 要 】

A tandem syn-selective conjugate addition - Nef reaction was observed when phenylnitromethane and oxygenated derivatives were allowed to react with an enoate derived from D-mannitol at rt in the presence of TBAF or DBU. While nitro-adducts predominate after 4h of reaction, the corresponding ketones were the main products after 12-24h of reaction. The Nef reaction occurred without racemization of the stereogenic center generated in the conjugate addition step.

【 授权许可】

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