Química Nova (Jan 2008)
Reação entre fenilnitrometanos e enoato derivado do D-manitol na presença de TBAF ou DBU: adição conjugada sin-seletiva e reação de NEF consecutiva 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
Abstract
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.
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