Repozytorium Uniwersytetu Jagiellońskiego
Organocatalytic syn-aldol reactions of hydroxy ketones with (S)-isoserinal : asymmetric synthesis of 6-deoxy-1,5-iminohexitols and related compounds
Organocatalytic syn-aldol reactions of hydroxy ketones ...
Opis pozycji
| tytuł: | Organocatalytic syn-aldol reactions of hydroxy ketones with (S)-isoserinal : asymmetric synthesis of 6-deoxy-1,5-iminohexitols and related compounds |
| autor: | Nicolas Cyril, Pluta Roman, Pasternak-Suder Monika  , Martin Olivier R., Młynarski Jacek
|
| tytuł czasopisma: | European Journal of Organic Chemistry |
| tom: | 2013 |
| numer: | 7 |
| data wydania: | 2013 |
| strony: | 1296-1305 |
| ISSN: |
1434-193X |
| eISSN: |
1099-0690 |
| DOI: | |
| uwagi: | Roman Pluta - Faculty of Chemistry, Jagiellonian University |
| język: | angielski |
| język czasopisma: | angielski |
| abstrakt w j. angielskim: | An improved and convenient preparation of protected ( S )- isoserinal on a large scale is reported. This key intermediate was reacted through organocatalyzed aldol reaction or Wittig based chain extension and functionalization to give enantio- pure 1,5,6-trideoxy-1,5-imino-hexitols such as 10a ( L - manno ) and 10b ( D - gluco ). These two compounds are of interest as glycosidase inhibitors. The elaborated organocatalytic pro-cess includes diastereoselective syn aldol reaction of ( S )-iso- serinal hydrate and hydroxyacetone or 1-hydroxy-2-oct- anone and is promoted by various amino acid-based cata- lysts. Diastereoselectivities of up to 8:1 were achieved, thus establishing a new, efficient synthetic route to these impor- tant carbohydrate mimics. |
| wydział:instytut/zakład/katedra: | Wydział Chemii : Zakład Chemii Organicznej |
| typ: | artykuł w czasopiśmie |
| podtyp: | artykuł |
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