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Volumn 62, Issue 11, 1997, Pages 3671-3677

Synthesis of L-daunosamine derivatives on the basis of the asymmetric dihydroxylation of 3-((E)-1-propenyl)-4,5-dihydroisoxazole

Author keywords

[No Author keywords available]

Indexed keywords

DAUNOSAMINE DERIVATIVE; ISOXAZOLE DERIVATIVE;

EID: 0030927650     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962293d     Document Type: Article
Times cited : (10)

References (36)
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    • For pertinent reviews, see: (a) Jäger, V.; Müller, I.; Leibold, T.; Hein, M.; Schwartz, M.; Fengler, M.; Jaraskova, L.; Pätzel, M.; LeRoy, P.-Y. J. Chem. Soc. Belg. 1994, 103, 491. (b) Hassner, A.; Murthy, K. S. K.; Maurya, R.; Dehaen, W.; Friedman, O. Lect. Heterocycl. Chem. 1994, 687. (c) Torssell, K. B. G. In Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; VCH: New York, 1988. (d) Curran, D. P. Adv. Cycloadd. 1988, 1, 129. (e) Kozikowski, A. P.; Chen, Y.-Y. Tetrahedron 1984, 40, 2345.
    • (1994) Lect. Heterocycl. Chem. , pp. 687
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    • For pertinent reviews, see: (a) Jäger, V.; Müller, I.; Leibold, T.; Hein, M.; Schwartz, M.; Fengler, M.; Jaraskova, L.; Pätzel, M.; LeRoy, P.-Y. J. Chem. Soc. Belg. 1994, 103, 491. (b) Hassner, A.; Murthy, K. S. K.; Maurya, R.; Dehaen, W.; Friedman, O. Lect. Heterocycl. Chem. 1994, 687. (c) Torssell, K. B. G. In Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; VCH: New York, 1988. (d) Curran, D. P. Adv. Cycloadd. 1988, 1, 129. (e) Kozikowski, A. P.; Chen, Y.-Y. Tetrahedron 1984, 40, 2345.
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    • For pertinent reviews, see: (a) Jäger, V.; Müller, I.; Leibold, T.; Hein, M.; Schwartz, M.; Fengler, M.; Jaraskova, L.; Pätzel, M.; LeRoy, P.-Y. J. Chem. Soc. Belg. 1994, 103, 491. (b) Hassner, A.; Murthy, K. S. K.; Maurya, R.; Dehaen, W.; Friedman, O. Lect. Heterocycl. Chem. 1994, 687. (c) Torssell, K. B. G. In Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; VCH: New York, 1988. (d) Curran, D. P. Adv. Cycloadd. 1988, 1, 129. (e) Kozikowski, A. P.; Chen, Y.-Y. Tetrahedron 1984, 40, 2345.
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    • For pertinent reviews, see: (a) Jäger, V.; Müller, I.; Leibold, T.; Hein, M.; Schwartz, M.; Fengler, M.; Jaraskova, L.; Pätzel, M.; LeRoy, P.-Y. J. Chem. Soc. Belg. 1994, 103, 491. (b) Hassner, A.; Murthy, K. S. K.; Maurya, R.; Dehaen, W.; Friedman, O. Lect. Heterocycl. Chem. 1994, 687. (c) Torssell, K. B. G. In Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; VCH: New York, 1988. (d) Curran, D. P. Adv. Cycloadd. 1988, 1, 129. (e) Kozikowski, A. P.; Chen, Y.-Y. Tetrahedron 1984, 40, 2345.
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    • For an account of our first attempts to perform AD reactions on alkene 2b, see ref 1b
    • (b) For an account of our first attempts to perform AD reactions on alkene 2b, see ref 1b.
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    • Assigned by analogy to 2-phenyl-4,5-cis-dimethyl-1,3-dioxalane diastereomers: Willy, W. E.; Binsch, G.; Eliel, E. E. J. Am. Chem. Soc., 1970, 92, 5394. Eliel, E. L.; Ko, K.-Y. Tetrahedron Lett. 1983, 24, 3547.
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    • Assigned by analogy to 2-phenyl-4,5-cis-dimethyl-1,3-dioxalane diastereomers: Willy, W. E.; Binsch, G.; Eliel, E. E. J. Am. Chem. Soc., 1970, 92, 5394. Eliel, E. L.; Ko, K.-Y. Tetrahedron Lett. 1983, 24, 3547.
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    • 4 showed variability of from 70:30 to 95:5 in the product diastereomer ratio: ref 1a
    • 4 showed variability of from 70:30 to 95:5 in the product diastereomer ratio: ref 1a.
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    • and references cited therein
    • Moses, S. R.; Wu, Y.-D.; Rondan, N. G.; Houk, K. N.; Schohe, R.; Jäger, V.; Fronczek, F. R. J. Am. Chem. Soc., 1984, 106, 3880. Attack anti-periplanar to the α-C,O-bond would be inconsistent with the observed major product: Kozikowski, A. P.; Ghosh, A. K. J. Am. Chem. Soc. 1982, 104, 5788 and references cited therein.
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    • Autoxidation of acetals: (a) Suzuki, M.; Inai, T.; Matsushima, R. Bull. Chem. Soc. Jpn. 1976, 49, 1585. (b) Kuramshin, E. M.; Kulak, L. G.; Nazarov, M. N.; Zlotsky, S. S. J. Prakt. Chem. 1989, 331, 591.
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    • See ref 3a, footnote 10
    • See ref 3a, footnote 10.
  • 36
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    • The author has deposited atomic coordinates for 4a with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK
    • The author has deposited atomic coordinates for 4a with the Cambridge Crystallographic Data Centre. The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.