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Volumn , Issue 5, 1999, Pages 632-634

A new diastereoselective synthesis of enantiomerically pure 1,2-oxazine derivatives by addition of lithiated methoxyallene to chiral nitrones

Author keywords

1,2 oxazine; Allenyl hydroxylamine; Methoxyallene; Nitrone

Indexed keywords

1,2 OXAZINE DERIVATIVE; 3,6 DIHYDRO 2H 1,2 OXAZINE; ALUMINUM CHLORIDE; HYDROXYLAMINE; LITHIATED METHOXYALLENE; NITROGEN DERIVATIVE; NITRONE; ORGANOLITHIUM COMPOUND; UNCLASSIFIED DRUG;

EID: 0032963762     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2662     Document Type: Article
Times cited : (86)

References (34)
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    • the authors suggest a two-step mechanism including a reverse Cope elimination
    • For cyclization of other α-allenylhydroxylamines to 3,6-dihydro-1,2-oxazine derivatives, see: E. Dumez, J.-P. Dulcére, Chem. Commun. 1998, 479-480; the authors suggest a two-step mechanism including a reverse Cope elimination.
    • (1998) Chem. Commun. , pp. 479-480
    • Dumez, E.1    Dulcére, J.-P.2
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    • note
    • 2Ph), 54.4 (q, OMe), 26.4, 25.4 (2 q, Me).
  • 31
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    • note
    • The byproduct may be formed by a retro-cne type reaction of the primary adduct. In several examples benzaldehyde oxime could be detected, which probably arises from nitrosomethylbenzene.
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    • Under these conditions compound 10a was converted into 11a with a synlanti ratio of approximately 70:30. For the discussion of the influence of protecting groups on the diastercoselectivity of serine derived nitrones see: P. Merino, S. Franco, F. L. Merchan, T. Tejero, J. Org. Chem. 1998, 63, 5627-5630.
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    • Merino, P.1    Franco, S.2    Merchan, F.L.3    Tejero, T.4
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    • note
    • The assignment is now proved by an X-ray crystal structure analysis of a subsequent product of anti-6b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.