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

Authors :: Vagner D. Pinho
Paulo R. R. Costa
Ayres G. Dias
Source :: Química Nova v.31 n.4 2008, Química Nova, Sociedade Brasileira de Química (SBQ), instacron:SBQ, Química Nova, Volume: 31, Issue: 4, Pages: 832-836, Published: 2008
Publication Year :: 2008
Publisher :: Sociedade Brasileira de Química, 2008.
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.

Subjects :: Nef reaction
Stereochemistry
Chemistry
stereoselective conjugate addition
General Chemistry
chiral enoates
Racemization
Stereocenter
Conjugate

Language :: Portuguese
Database :: OpenAIRE
Journal :: Química Nova v.31 n.4 2008, Química Nova, Sociedade Brasileira de Química (SBQ), instacron:SBQ, Química Nova, Volume: 31, Issue: 4, Pages: 832-836, Published: 2008
Accession number :: edsair.doi.dedup.....2507c5ff85639cd4c2c3a45875e3454b

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