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EnglishThe four-step conversion of a series of N-Boc-protected l-amino acid methyl esters into enantiopure N-Boc allylamines by a modified Julia olefination is described. Key steps include the reaction of a lithiated phenylalkylsulfone with amino esters, giving chiral β-ketosulfones, and the reductive elimination of related α-acetoxysulfones. The overall transformation takes place under mild conditions, with good yields, and without loss of stereochemical integrity, being in this respect superior to the conventional Julia reaction of α-amino aldehydes.
| Titolo: | Synthesis of chiral, enantiopure allylic amines by the Julia olefination of α-amino esters |
| Autori: | |
| Data di pubblicazione: | 2016 |
| Rivista: | |
| Abstract: | The four-step conversion of a series of N-Boc-protected l-amino acid methyl esters into enantiopure N-Boc allylamines by a modified Julia olefination is described. Key steps include the reaction of a lithiated phenylalkylsulfone with amino esters, giving chiral β-ketosulfones, and the reductive elimination of related α-acetoxysulfones. The overall transformation takes place under mild conditions, with good yields, and without loss of stereochemical integrity, being in this respect superior to the conventional Julia reaction of α-amino aldehydes. |
| Handle: | http://hdl.handle.net/11368/2877016 |
| Digital Object Identifier (DOI): | http://dx.doi.org/10.3390/molecules21060805 |
| URL: | http://www.mdpi.com/1420-3049/21/6/805 |
| Appare nelle tipologie: | 1.1 Articolo in Rivista |
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| File | Descrizione | Tipologia | Licenza | |
|---|---|---|---|---|
| 2016_Molecules-21-00805-2.pdf | Documento in Versione Editoriale | Digital Rights Management non definito | Open Access Visualizza/Apri | |
| molecules-21-00805-s001.pdf | Supplementary material | Altro materiale allegato | Digital Rights Management non definito | Open Access Visualizza/Apri |
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