Synthesis of new chiral auxiliares from carbohydrates for Et2AlCl-promoted Diels-Alder reactions
Acrylates 3-O-acryloyl-4,5-di-O-benzoyl-1,2- O-isopropylidene-beta-D-fructopyranose (6) and 3-O-benzyl-5-O-acryloyl-1,2-O -isopropylidene-alpha-D-xylofuranose (8) were synthesized in few steps from carbohydrates to construct chiral dienophiles for asymmetric Diels-Alder reaction with cyclopentadiene...
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| Format: | Article |
| Language: | English |
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Sociedade Brasileira de Química
2000-01-01
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| Series: | Journal of the Brazilian Chemical Society |
| Subjects: | |
| Online Access: | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532000000300012 |
| _version_ | 1811290035416203264 |
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| author | Ferreira Vitor F. Pinheiro Sergio Perrone Clarissa C. Costa Paulo R. R. |
| author_facet | Ferreira Vitor F. Pinheiro Sergio Perrone Clarissa C. Costa Paulo R. R. |
| author_sort | Ferreira Vitor F. |
| collection | DOAJ |
| description | Acrylates 3-O-acryloyl-4,5-di-O-benzoyl-1,2- O-isopropylidene-beta-D-fructopyranose (6) and 3-O-benzyl-5-O-acryloyl-1,2-O -isopropylidene-alpha-D-xylofuranose (8) were synthesized in few steps from carbohydrates to construct chiral dienophiles for asymmetric Diels-Alder reaction with cyclopentadiene under thermal and Et2AlCl-promoted conditions. Although from moderate to excellent endo/exo ratios were obtained, low p-facial diastereoselectivities were observed for the cycloadducts 3-O-[(1'R, 4'R)-bicyclo-[2.2.1]hept-2'-ene-5'-formyl]-4,5-di- O-benzoyl-1,2-O-isopropylidene-beta-D-fructopyranose (21a) and 3-O-benzyl-5-O-[(1'S, 4'S)-bicyclo-[2.2.1]hept-2'-ene-5'-formyl]-1,2- O-isopropylideno-alpha-D-yilofuranose (22b) indicating that pi-stacked conformations in the Lewis acid-acrylates complex were not effective. |
| first_indexed | 2024-04-13T04:05:52Z |
| format | Article |
| id | doaj.art-be6f8d7f08c147e1b4a25437e2bcb28d |
| institution | Directory Open Access Journal |
| issn | 0103-5053 |
| language | English |
| last_indexed | 2024-04-13T04:05:52Z |
| publishDate | 2000-01-01 |
| publisher | Sociedade Brasileira de Química |
| record_format | Article |
| series | Journal of the Brazilian Chemical Society |
| spelling | doaj.art-be6f8d7f08c147e1b4a25437e2bcb28d2022-12-22T03:03:18ZengSociedade Brasileira de QuímicaJournal of the Brazilian Chemical Society0103-50532000-01-01113266273Synthesis of new chiral auxiliares from carbohydrates for Et2AlCl-promoted Diels-Alder reactionsFerreira Vitor F.Pinheiro SergioPerrone Clarissa C.Costa Paulo R. R.Acrylates 3-O-acryloyl-4,5-di-O-benzoyl-1,2- O-isopropylidene-beta-D-fructopyranose (6) and 3-O-benzyl-5-O-acryloyl-1,2-O -isopropylidene-alpha-D-xylofuranose (8) were synthesized in few steps from carbohydrates to construct chiral dienophiles for asymmetric Diels-Alder reaction with cyclopentadiene under thermal and Et2AlCl-promoted conditions. Although from moderate to excellent endo/exo ratios were obtained, low p-facial diastereoselectivities were observed for the cycloadducts 3-O-[(1'R, 4'R)-bicyclo-[2.2.1]hept-2'-ene-5'-formyl]-4,5-di- O-benzoyl-1,2-O-isopropylidene-beta-D-fructopyranose (21a) and 3-O-benzyl-5-O-[(1'S, 4'S)-bicyclo-[2.2.1]hept-2'-ene-5'-formyl]-1,2- O-isopropylideno-alpha-D-yilofuranose (22b) indicating that pi-stacked conformations in the Lewis acid-acrylates complex were not effective.http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532000000300012asymmetric Diels-Alder reactionschiral dienophilescarbohydrates |
| spellingShingle | Ferreira Vitor F. Pinheiro Sergio Perrone Clarissa C. Costa Paulo R. R. Synthesis of new chiral auxiliares from carbohydrates for Et2AlCl-promoted Diels-Alder reactions Journal of the Brazilian Chemical Society asymmetric Diels-Alder reactions chiral dienophiles carbohydrates |
| title | Synthesis of new chiral auxiliares from carbohydrates for Et2AlCl-promoted Diels-Alder reactions |
| title_full | Synthesis of new chiral auxiliares from carbohydrates for Et2AlCl-promoted Diels-Alder reactions |
| title_fullStr | Synthesis of new chiral auxiliares from carbohydrates for Et2AlCl-promoted Diels-Alder reactions |
| title_full_unstemmed | Synthesis of new chiral auxiliares from carbohydrates for Et2AlCl-promoted Diels-Alder reactions |
| title_short | Synthesis of new chiral auxiliares from carbohydrates for Et2AlCl-promoted Diels-Alder reactions |
| title_sort | synthesis of new chiral auxiliares from carbohydrates for et2alcl promoted diels alder reactions |
| topic | asymmetric Diels-Alder reactions chiral dienophiles carbohydrates |
| url | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532000000300012 |
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