Indução assimétrica 1,5-Anti na adição de enolatos de boro de metilcetonas beta-oxigenadas a aldeídos 1,5-Asymmetric induction in the boron-mediated aldol reaction of beta-oxygenated methyl ketones
<abstract language="eng">High levels of substrate-based 1,5-stereoinduction are obtained in the boron-mediated aldol reactions of beta-oxygenated methyl ketones with achiral and chiral aldehydes. Remote induction from the boron enolates gives the 1,5-anti adducts, with the enolate pi...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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Sociedade Brasileira de Química
2007-01-01
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| Series: | Química Nova |
| Subjects: | |
| Online Access: | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422007000800036 |
| _version_ | 1811192924072837120 |
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| author | Luiz C. Dias Andrea M. Aguilar |
| author_facet | Luiz C. Dias Andrea M. Aguilar |
| author_sort | Luiz C. Dias |
| collection | DOAJ |
| description | <abstract language="eng">High levels of substrate-based 1,5-stereoinduction are obtained in the boron-mediated aldol reactions of beta-oxygenated methyl ketones with achiral and chiral aldehydes. Remote induction from the boron enolates gives the 1,5-anti adducts, with the enolate pi-facial selectivity critically dependent upon the nature of the beta-alkoxy protecting group. This 1,5-anti aldol methodology has been strategically employed in the total synthesis of several natural products. At present, the origin of the high level of 1,5-anti induction obtained with the boron enolates is unclear, although a model based on a hydrogen bonding between the alkoxy oxygen and the formyl hydrogen has been recently proposed. |
| first_indexed | 2024-04-11T23:59:14Z |
| format | Article |
| id | doaj.art-8834c163142a400d88faa5be4eebd8ae |
| institution | Directory Open Access Journal |
| issn | 0100-4042 1678-7064 |
| language | English |
| last_indexed | 2024-04-11T23:59:14Z |
| publishDate | 2007-01-01 |
| publisher | Sociedade Brasileira de Química |
| record_format | Article |
| series | Química Nova |
| spelling | doaj.art-8834c163142a400d88faa5be4eebd8ae2022-12-22T03:56:16ZengSociedade Brasileira de QuímicaQuímica Nova0100-40421678-70642007-01-013082007201510.1590/S0100-40422007000800036Indução assimétrica 1,5-Anti na adição de enolatos de boro de metilcetonas beta-oxigenadas a aldeídos 1,5-Asymmetric induction in the boron-mediated aldol reaction of beta-oxygenated methyl ketonesLuiz C. DiasAndrea M. Aguilar<abstract language="eng">High levels of substrate-based 1,5-stereoinduction are obtained in the boron-mediated aldol reactions of beta-oxygenated methyl ketones with achiral and chiral aldehydes. Remote induction from the boron enolates gives the 1,5-anti adducts, with the enolate pi-facial selectivity critically dependent upon the nature of the beta-alkoxy protecting group. This 1,5-anti aldol methodology has been strategically employed in the total synthesis of several natural products. At present, the origin of the high level of 1,5-anti induction obtained with the boron enolates is unclear, although a model based on a hydrogen bonding between the alkoxy oxygen and the formyl hydrogen has been recently proposed.http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-404220070008000361,5-anti inductionboron enolatesaldol reactions |
| spellingShingle | Luiz C. Dias Andrea M. Aguilar Indução assimétrica 1,5-Anti na adição de enolatos de boro de metilcetonas beta-oxigenadas a aldeídos 1,5-Asymmetric induction in the boron-mediated aldol reaction of beta-oxygenated methyl ketones Química Nova 1,5-anti induction boron enolates aldol reactions |
| title | Indução assimétrica 1,5-Anti na adição de enolatos de boro de metilcetonas beta-oxigenadas a aldeídos 1,5-Asymmetric induction in the boron-mediated aldol reaction of beta-oxygenated methyl ketones |
| title_full | Indução assimétrica 1,5-Anti na adição de enolatos de boro de metilcetonas beta-oxigenadas a aldeídos 1,5-Asymmetric induction in the boron-mediated aldol reaction of beta-oxygenated methyl ketones |
| title_fullStr | Indução assimétrica 1,5-Anti na adição de enolatos de boro de metilcetonas beta-oxigenadas a aldeídos 1,5-Asymmetric induction in the boron-mediated aldol reaction of beta-oxygenated methyl ketones |
| title_full_unstemmed | Indução assimétrica 1,5-Anti na adição de enolatos de boro de metilcetonas beta-oxigenadas a aldeídos 1,5-Asymmetric induction in the boron-mediated aldol reaction of beta-oxygenated methyl ketones |
| title_short | Indução assimétrica 1,5-Anti na adição de enolatos de boro de metilcetonas beta-oxigenadas a aldeídos 1,5-Asymmetric induction in the boron-mediated aldol reaction of beta-oxygenated methyl ketones |
| title_sort | inducao assimetrica 1 5 anti na adicao de enolatos de boro de metilcetonas beta oxigenadas a aldeidos 1 5 asymmetric induction in the boron mediated aldol reaction of beta oxygenated methyl ketones |
| topic | 1,5-anti induction boron enolates aldol reactions |
| url | http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0100-40422007000800036 |
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