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Volumn 2, Issue 20, 2000, Pages 3165-3168

First asymmetric Hetero Diels-Alder reaction of 1-sulfinyl dienes with nitroso derivatives. A new entry to the synthesis of optically pure 1,4-imino-L-ribitol derivatives

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ENZYME INHIBITOR; GLYCOSIDASE; NITROSO DERIVATIVE; RIBITOL;

EID: 0034609698     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0063611     Document Type: Article
Times cited : (43)

References (64)
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    • note
    • 2-), 89.6 (C6), 117.1 (C4), 125.9, 128.1, 128.4, 128.6, 129.3 (HC-arom), 133.7 (C5), 134.8, 135.5, 142.4 (C-arom), 155.1 (C=O).
  • 57
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    • This interaction, which is similar to the allylic strain, must also be responsible for the preferred axial orientation of the phenyl group (bulkier than the methyl one) in N-alkoxycarbonyl derivatives of 3-phenyl 1,4-thiazanes (García Ruano, J. L.; Martinez, M. C.; Rodriguez, J. H.; Olefirowicz, E. M.; Eliel, E. L. J. Org. Chem. 1992, 57, 4215).
    • (1992) J. Org. Chem. , vol.57 , pp. 4215
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    • A small amount (18%) of N-benzyloxycarbonyl 5-methylpyrrolin-2(5H)-one was also isolated. Its formation from 3 can be rationalized according to a similar evolution to that described for Firl and Kresce for other oxazine derivatives bearing electron-withdrawing groups at C-6, which are transformed into pyrrolinone derivatives by treating with base (Firl, J.; Kresce, G. Chem. Ber. 1966, 99, 3695. Defoin, A.; Geffroy, G.; Le Nouen, D.; Spileers, D.; Streth, J. Helv. Chim. Acta 1988, 71, 1642).
    • (1966) Chem. Ber. , vol.99 , pp. 3695
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  • 59
    • 0000416867 scopus 로고
    • A small amount (18%) of N-benzyloxycarbonyl 5-methylpyrrolin-2(5H)-one was also isolated. Its formation from 3 can be rationalized according to a similar evolution to that described for Firl and Kresce for other oxazine derivatives bearing electron-withdrawing groups at C-6, which are transformed into pyrrolinone derivatives by treating with base (Firl, J.; Kresce, G. Chem. Ber. 1966, 99, 3695. Defoin, A.; Geffroy, G.; Le Nouen, D.; Spileers, D.; Streth, J. Helv. Chim. Acta 1988, 71, 1642).
    • (1988) Helv. Chim. Acta , vol.71 , pp. 1642
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  • 61
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    • Morrison, J. D., Ed.; Academic Press: New York
    • (b) Yamaguchi, S. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1983; Vol. 1, p 125.
    • (1983) Asymmetric Synthesis , vol.1 , pp. 125
    • Yamaguchi, S.1
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    • note
    • 7S 462.158649, found 462.157129.
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    • note
    • -3.
  • 64
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    • note
    • 1H NMR signals corresponding to Me-C2, H-C5, and H-C2 appear as a serie of two sets of same intensity signals when the spectrum is registered at temperature below 50°C.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.