ChemInform Abstract: Asymmetric Synthesis of (S)-α-Methyl α-Amino Acids by Alkylation of Chiral 3,6-Dihydro-2H-1,4-oxazin-2-ones Using Unactivated Alkyl Halides and Organic Bases
In: ChemInform, Jg. 30 (2010-06-17)
Online
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Zugriff:
3,6-Dihydro-2H-1,4-oxazin-2-ones 1 have been diastereoselectively (>96% de) alkylated using unactivated alkyl halides and organic bases such as 2-tert-butylimino-2-diethylamino-1,3-dimethylperhydro-1,3,2-diazaphosphorine (BEMP) or 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) at room temperature in the presence of LiI. Hydrolysis of the resulting alkylated systems afforded enantiomerically enriched (S)-α-methyl α-amino acids. When 1,3-diiodopropane was used, spontaneous N-alkylation also took place giving bicyclic oxazinone 6 which was hydrolyzed to (S)-α-methylproline.
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ChemInform Abstract: Asymmetric Synthesis of (S)-α-Methyl α-Amino Acids by Alkylation of Chiral 3,6-Dihydro-2H-1,4-oxazin-2-ones Using Unactivated Alkyl Halides and Organic Bases
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| Autor/in / Beteiligte Person: | Galindo, Nuria ; Chinchilla, Rafael ; Nájera, Carmen |
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| Zeitschrift: | ChemInform, Jg. 30 (2010-06-17) |
| Veröffentlichung: | Wiley, 2010 |
| Medientyp: | unknown |
| ISSN: | 1522-2667 (print) ; 0931-7597 (print) |
| DOI: | 10.1002/chin.199904163 |
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