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Volumn 41, Issue 17, 1985, Pages 3519-3528

Synthesis of amino sugars via isoxazolines. Nitrile oxide-furan adducts as key intermediates in the isoxazoline route towards novel amino sugar derivatives

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EID: 0000720870     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)96705-5     Document Type: Article
Times cited : (109)

References (82)
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  • 5
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    • Eliminierende Ringöffnung von 2-Isoxazolinen: ein neuer Weg zu α,β-ungesättigten Ketonen
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  • 7
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    • Aldolkondensation mit hoher Stereoselektivität durch Verwendung eines enantioselektiven chiralen Enolats
    • For a discussion on the use of syn/anti stereodescriptors see
    • (1980) Angewandte Chemie , vol.91 , pp. 573
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  • 13
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    • 4-Hydroxylierung von Isoxazolinen; Synthese vonrac-Phytosphingosin (ribo-2-Amino-1,3,4-octadecantriol)
    • (1981) Angewandte Chemie , vol.93 , pp. 578
    • Schwab1    Jäger2
  • 15
  • 16
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    • Modellreaktionen zur stereokontrollierten Synthese von Aminopolyolen; Reduktion von Isoxazolinen mit freier oder geschützter Hydroxygruppe in 4-Position oder in Seitenketten
    • (1981) Angewandte Chemie , vol.93 , pp. 576
    • Jäger1    Schwab2    Buß3
  • 25
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    • P. Caramella and P. Grünanger in Ref. 15b, Vol. 1, Chap. 3, p. 291.
  • 27
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    • R. Huisgen in Ref. 15b, Vol. 1. Chap. 1, p. 1.
  • 28
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    • K.N. Houk and K. Yamaguchi in Ref. 15b, Vol. 2, Chap. 13, p. 407.
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    • and Ref. 12 (Christl).
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    • On longer reaction times, the isocyanate dehydrating agent is consumed slowly, probably due to oligomerization by the tertiary amine. Further, isocyanate slowly adds N,N'-diphenylurea, Universität Gießen
    • (1978) Dissertation
    • Günther1
  • 40
    • 0019959484 scopus 로고
    • A related approach to amino sugars, using optically active N-glycosyl nitrone/furan cycloadducts, was developed by Prof. Vasella. In a stereochemically complementary way, this led to the synthesis of D-nojirimycin
    • (1982) Helv. Chim. Acta , vol.65 , pp. 1134
    • Vasella1    Voeffray2
  • 41
    • 0009712031 scopus 로고
    • A related approach to amino sugars, using optically active N-glycosyl nitrone/furan cycloadducts, was developed by Prof. Vasella. In a stereochemically complementary way, this led to the synthesis of D-nojirimycin, Universität Zürich
    • (1983) Dissertation
    • Voeffray1
  • 43
    • 33845554224 scopus 로고
    • For other nitrone-based routes to amino sugars, via 4-oxygenated isoxazolidines, see
    • (1982) J. Org. Chem. , vol.47 , pp. 2047
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  • 50
    • 0009483240 scopus 로고
    • use of furan-aldehyde photocycloadditions in carbo-hydrate synthesis
    • Cf.
    • (1983) Tetrahedron , vol.39 , pp. 805
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  • 55
    • 84918087456 scopus 로고    scopus 로고
    • see also Ref. 26
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    • 0002642584 scopus 로고
    • The development of polyquinane chemistry
    • Cf. all-carbon analogues
    • (1979) Top Curr. Chem. , vol.79 , pp. 41
    • Paquette1
  • 69
    • 84981375171 scopus 로고
    • Synthesen mit Isoxazolinen, 5. 1,3-Asymmetrische Induktion bei der Reduktion 3,5-disubstituierter 2-Isoxazoline; diastereoselektive Synthese und Konfigurationszuordnung von γ-Aminoalkoholen
    • (1980) Liebigs Annalen der Chemie , pp. 101
    • Jäger1    Buß2
  • 70
    • 84981454264 scopus 로고
    • Synthesen mit Isoxazolinen, 6. Asymmetrische Induktion bei der Reduktion von 2-Isoxazolinen zu γ-Aminoalkoholen mit zwei und drei benachbarten Stereozentren2,3)
    • (1980) Liebigs Annalen der Chemie , pp. 122
    • Jäger1    Büß2    Schwab3
  • 71
    • 0001316756 scopus 로고
    • Stereocontrol in isoxazoline reductions. Synthesis of aminodeoxy-DL-xylo- and arabino-pentose derivatives from furoisoxazolines
    • (1985) Tetrahedron Letters , pp. 2997
    • Jäger1    Müller2    Paulus3
  • 74
    • 77955663073 scopus 로고
    • These rules apparently apply also to the case of 1,3-diols, in press. We thank Prof. Hoffmann, Marburg, for a preprint of this work.
    • (1985) Chem. Ber.
    • Hoffmann1    Weidmann2
  • 77
    • 84918087455 scopus 로고    scopus 로고
    • W. Schwab and V. Jäger, unpublished results (1980/1)
  • 79
    • 84918087454 scopus 로고    scopus 로고
    • B. Häfele and V. Jäger, unpublished results (1984).
  • 80
    • 84918087453 scopus 로고    scopus 로고
    • 3 ; Br/Br; Br/OR ; I/OR) occur with similar high stereoselectivity : Ref. 4 ; presented at the 3rd Convegno Sulle Reazioni Pericicliche, Naples, October (1984).
  • 81
    • 84985218926 scopus 로고
    • A Convenient Synthesis of Nitroacetaldehyde Dialkylacetals
    • (1981) Synthesis , pp. 878
    • René1    Royer2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.