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Volumn 74, Issue 15, 2009, Pages 5510-5515

Oxazoline-oxazinone oxidative rearrangement. Divergent syntheses of (2S,3S)-4,4,4-trifluorovaline and (2S,4S)-5,5,5-trifluoroleucine

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL EQUATIONS; CONFIGURATIONALLY; DIVERGENT SYNTHESIS; ENAMINES; HYDROCHLORIDE SALTS; OXAZINONES; OXAZOLINES; OXIDATIVE REARRANGEMENTS; SELECTIVE HYDROGENATION; STEREOSELECTIVE SYNTHESIS;

EID: 68049142866     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo900654y     Document Type: Article
Times cited : (27)

References (56)
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  • 25
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    • Nucleophilic addition to oxazinones: (g) Tohma, S.; Rikimaru, K.; Endo, A.; Shimamoto, K.; Kan, T.; Fukuyama, T. Synthesis 2004, 909.
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  • 31
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    • Cycloadditions onto morpholinone-derived ylides or oxazinones: (m) Harwood, L. M.; Macro, J.; Watkin, D.; Williams, C. E.; Wong, L. F. Tetrahedron: Asymmetry 1992, 3, 1127.
    • Cycloadditions onto morpholinone-derived ylides or oxazinones: (m) Harwood, L. M.; Macro, J.; Watkin, D.; Williams, C. E.; Wong, L. F. Tetrahedron: Asymmetry 1992, 3, 1127.
  • 34
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    • Radical addition to oxazinones: (p) Bertrand, M. P.; Feray, L.; Nouguier, R.; Stella, L. Synlett 1998, 780.
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    • Optically enriched 7: (c) Uemura, T.; Zhang, X.; Matsumura, K.; Sayo, N.; Kumobayashi, H.; Ohta, T.; Nozaki, K.; Takaya, H. J. Org. Chem. 1996, 61, 5510.
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    • The trans configuration of the double bond was assigned based on the absence of NOE enhancements in either the methyl or vinyl proton upon irradiation of the other signal.
    • The trans configuration of the double bond was assigned based on the absence of NOE enhancements in either the methyl or vinyl proton upon irradiation of the other signal.
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    • For the procedure, see
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    • For the optical rotation of (R)-phenylglycinol, see: Garcia Ruano, J. L.; Alcudia, A.; Del Prado, M.; Barros, D.; Maestro, M. C.; Fernandez, I. J. Org. Chem. 2000, 65, 2856.
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    • 2 signals adjacent to the C=N bond, suggesting that a second oxidation took place at this position at higher temperature and longer reaction times. Reaction times of less than 5 min returned only starting material, suggesting a short induction period.
    • 2 signals adjacent to the C=N bond, suggesting that a second oxidation took place at this position at higher temperature and longer reaction times. Reaction times of less than 5 min returned only starting material, suggesting a short induction period.


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