The reaction between Phenylnitromethanes and enoate derived from D-mannitol in the presence of TBAF or DBU: tandem syn-selective conjugate addition and NEF reaction

Química Nova

Centro de Ciências da Saúde, Rio de Janeiro, Brasil¹  Dias, Ayres G.¹  Pinho, Vagner D.¹  Costa, Paulo R. R.¹  Universidade do Estado do Rio de Janeiro, Rio de Janeiro, Brasil¹ 

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

DOI  :  10.1590/S0100-40422008000400024

学科分类：化学（综合）

来源: Sociedade Brasileira de Quimica

【 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】

Unknown