Unusual Regioselectivity in the Opening of Epoxides by Carboxylic Acid Enediolates
Addition of carboxylic acid dianions appears to be a potential alternative to the use of aluminium enolates for nucleophilic ring opening of epoxides. These conditions require the use of a sub-stoichiometric amount of amine (10% mol) for dianion generation and the previous activation of the epoxide...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2008-06-01
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| Series: | Molecules |
| Subjects: | |
| Online Access: | http://www.mdpi.com/1420-3049/13/6/1303/ |
| _version_ | 1828760152503746560 |
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| author | José Segura Margarita Parra Salvador Gil Luis R. Domingo |
| author_facet | José Segura Margarita Parra Salvador Gil Luis R. Domingo |
| author_sort | José Segura |
| collection | DOAJ |
| description | Addition of carboxylic acid dianions appears to be a potential alternative to the use of aluminium enolates for nucleophilic ring opening of epoxides. These conditions require the use of a sub-stoichiometric amount of amine (10% mol) for dianion generation and the previous activation of the epoxide with LiCl. Yields are good, with high regioselectivity, but the use of styrene oxide led, unexpectedly, to a mixture resulting from the attack on both the primary and secondary carbon atoms. Generally, a low diastereoselectivity is seen on attack at the primary center, however only one diastereoisomer was obtained from attack to the secondary carbon of the styrene oxide. |
| first_indexed | 2024-12-11T01:09:23Z |
| format | Article |
| id | doaj.art-1285d7b7838542388db3b6d8457bfd41 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T01:09:23Z |
| publishDate | 2008-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-1285d7b7838542388db3b6d8457bfd412022-12-22T01:26:05ZengMDPI AGMolecules1420-30492008-06-011361303131110.3390/molecules13061303Unusual Regioselectivity in the Opening of Epoxides by Carboxylic Acid EnediolatesJosé SeguraMargarita ParraSalvador GilLuis R. DomingoAddition of carboxylic acid dianions appears to be a potential alternative to the use of aluminium enolates for nucleophilic ring opening of epoxides. These conditions require the use of a sub-stoichiometric amount of amine (10% mol) for dianion generation and the previous activation of the epoxide with LiCl. Yields are good, with high regioselectivity, but the use of styrene oxide led, unexpectedly, to a mixture resulting from the attack on both the primary and secondary carbon atoms. Generally, a low diastereoselectivity is seen on attack at the primary center, however only one diastereoisomer was obtained from attack to the secondary carbon of the styrene oxide.http://www.mdpi.com/1420-3049/13/6/1303/Lactoneslithium chloridenucleophilic additionregioselectivitydiastereoselectivity. |
| spellingShingle | José Segura Margarita Parra Salvador Gil Luis R. Domingo Unusual Regioselectivity in the Opening of Epoxides by Carboxylic Acid Enediolates Molecules Lactones lithium chloride nucleophilic addition regioselectivity diastereoselectivity. |
| title | Unusual Regioselectivity in the Opening of Epoxides by Carboxylic Acid Enediolates |
| title_full | Unusual Regioselectivity in the Opening of Epoxides by Carboxylic Acid Enediolates |
| title_fullStr | Unusual Regioselectivity in the Opening of Epoxides by Carboxylic Acid Enediolates |
| title_full_unstemmed | Unusual Regioselectivity in the Opening of Epoxides by Carboxylic Acid Enediolates |
| title_short | Unusual Regioselectivity in the Opening of Epoxides by Carboxylic Acid Enediolates |
| title_sort | unusual regioselectivity in the opening of epoxides by carboxylic acid enediolates |
| topic | Lactones lithium chloride nucleophilic addition regioselectivity diastereoselectivity. |
| url | http://www.mdpi.com/1420-3049/13/6/1303/ |
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