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 language="eng">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 4...
| Main Authors: | , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
Sociedade Brasileira de Química
2008-01-01
|
| Series: | Química Nova |
| Subjects: | |
| Online Access: | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422008000400024 |
| _version_ | 1828977153177288704 |
|---|---|
| author | Ayres G. Dias Vagner D. Pinho Paulo R. R. Costa |
| author_facet | Ayres G. Dias Vagner D. Pinho Paulo R. R. Costa |
| author_sort | Ayres G. Dias |
| collection | DOAJ |
| description | <abstract language="eng">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. |
| first_indexed | 2024-12-14T14:53:04Z |
| format | Article |
| id | doaj.art-246b04f898e744ecbd0ad142ee70d726 |
| institution | Directory Open Access Journal |
| issn | 0100-4042 1678-7064 |
| language | English |
| last_indexed | 2024-12-14T14:53:04Z |
| publishDate | 2008-01-01 |
| publisher | Sociedade Brasileira de Química |
| record_format | Article |
| series | Química Nova |
| spelling | doaj.art-246b04f898e744ecbd0ad142ee70d7262022-12-21T22:57:05ZengSociedade Brasileira de QuímicaQuímica Nova0100-40421678-70642008-01-0131483283610.1590/S0100-40422008000400024Reação 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 reactionAyres G. DiasVagner D. PinhoPaulo R. R. Costa<abstract language="eng">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.http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422008000400024Nef reactionchiral enoatesstereoselective conjugate addition |
| spellingShingle | Ayres G. Dias Vagner D. Pinho Paulo R. R. Costa 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 Química Nova Nef reaction chiral enoates stereoselective conjugate addition |
| title | 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 |
| title_full | 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 |
| title_fullStr | 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 |
| title_full_unstemmed | 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 |
| title_short | 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 |
| title_sort | reacao entre fenilnitrometanos e enoato derivado do d manitol na presenca de tbaf ou dbu adicao conjugada sin seletiva e reacao 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 |
| topic | Nef reaction chiral enoates stereoselective conjugate addition |
| url | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422008000400024 |
| work_keys_str_mv | AT ayresgdias reacaoentrefenilnitrometanoseenoatoderivadododmanitolnapresencadetbafoudbuadicaoconjugadasinseletivaereacaodenefconsecutivathereactionbetweenphenylnitromethanesandenoatederivedfromdmannitolinthepresenceoftbafordbutandemsynselectiveconjugateadditionandnefr AT vagnerdpinho reacaoentrefenilnitrometanoseenoatoderivadododmanitolnapresencadetbafoudbuadicaoconjugadasinseletivaereacaodenefconsecutivathereactionbetweenphenylnitromethanesandenoatederivedfromdmannitolinthepresenceoftbafordbutandemsynselectiveconjugateadditionandnefr AT paulorrcosta reacaoentrefenilnitrometanoseenoatoderivadododmanitolnapresencadetbafoudbuadicaoconjugadasinseletivaereacaodenefconsecutivathereactionbetweenphenylnitromethanesandenoatederivedfromdmannitolinthepresenceoftbafordbutandemsynselectiveconjugateadditionandnefr |