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1
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49049130382
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Synthesis of amino sugars via isoxazolines the concept and one application: nitrile oxide/furan adducts
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Preliminary communication
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(1982)
Tetrahedron Letters
, pp. 4777
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Müller1
Jäger2
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5
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24444476132
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Eliminierende Ringöffnung von 2-Isoxazolinen: ein neuer Weg zu α,β-ungesättigten Ketonen
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(1976)
Angewandte Chemie
, vol.88
, pp. 27
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Jäger1
Grund2
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7
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0009529363
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Aldolkondensation mit hoher Stereoselektivität durch Verwendung eines enantioselektiven chiralen Enolats
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For a discussion on the use of syn/anti stereodescriptors see
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(1980)
Angewandte Chemie
, vol.91
, pp. 573
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Masumune1
Ali2
Snitman3
Garvey4
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13
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0008823670
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4-Hydroxylierung von Isoxazolinen; Synthese vonrac-Phytosphingosin (ribo-2-Amino-1,3,4-octadecantriol)
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(1981)
Angewandte Chemie
, vol.93
, pp. 578
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-
Schwab1
Jäger2
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16
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0001518014
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Modellreaktionen zur stereokontrollierten Synthese von Aminopolyolen; Reduktion von Isoxazolinen mit freier oder geschützter Hydroxygruppe in 4-Position oder in Seitenketten
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(1981)
Angewandte Chemie
, vol.93
, pp. 576
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-
Jäger1
Schwab2
Buß3
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25
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84918087463
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P. Caramella and P. Grünanger in Ref. 15b, Vol. 1, Chap. 3, p. 291.
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27
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84918087462
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R. Huisgen in Ref. 15b, Vol. 1. Chap. 1, p. 1.
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28
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84918087461
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K.N. Houk and K. Yamaguchi in Ref. 15b, Vol. 2, Chap. 13, p. 407.
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35
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84918087459
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and Ref. 12 (Christl).
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36
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84914202563
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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
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(1978)
Dissertation
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Günther1
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40
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0019959484
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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
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(1982)
Helv. Chim. Acta
, vol.65
, pp. 1134
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Vasella1
Voeffray2
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41
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0009712031
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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
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(1983)
Dissertation
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Voeffray1
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43
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33845554224
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For other nitrone-based routes to amino sugars, via 4-oxygenated isoxazolidines, see
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(1982)
J. Org. Chem.
, vol.47
, pp. 2047
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Dicken1
DeShong2
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50
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0009483240
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use of furan-aldehyde photocycloadditions in carbo-hydrate synthesis
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Cf.
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(1983)
Tetrahedron
, vol.39
, pp. 805
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Kozluk1
Zamojski2
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55
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84918087456
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see also Ref. 26
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64
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0002642584
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The development of polyquinane chemistry
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Cf. all-carbon analogues
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(1979)
Top Curr. Chem.
, vol.79
, pp. 41
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Paquette1
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69
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84981375171
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Synthesen mit Isoxazolinen, 5. 1,3-Asymmetrische Induktion bei der Reduktion 3,5-disubstituierter 2-Isoxazoline; diastereoselektive Synthese und Konfigurationszuordnung von γ-Aminoalkoholen
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(1980)
Liebigs Annalen der Chemie
, pp. 101
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Jäger1
Buß2
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70
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84981454264
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Synthesen mit Isoxazolinen, 6. Asymmetrische Induktion bei der Reduktion von 2-Isoxazolinen zu γ-Aminoalkoholen mit zwei und drei benachbarten Stereozentren2,3)
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(1980)
Liebigs Annalen der Chemie
, pp. 122
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Jäger1
Büß2
Schwab3
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71
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0001316756
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Stereocontrol in isoxazoline reductions. Synthesis of aminodeoxy-DL-xylo- and arabino-pentose derivatives from furoisoxazolines
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(1985)
Tetrahedron Letters
, pp. 2997
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Jäger1
Müller2
Paulus3
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74
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77955663073
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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.
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(1985)
Chem. Ber.
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Hoffmann1
Weidmann2
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77
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84918087455
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W. Schwab and V. Jäger, unpublished results (1980/1)
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79
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84918087454
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B. Häfele and V. Jäger, unpublished results (1984).
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80
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84918087453
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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).
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81
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84985218926
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A Convenient Synthesis of Nitroacetaldehyde Dialkylacetals
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(1981)
Synthesis
, pp. 878
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René1
Royer2
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