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Volumn 63, Issue 11, 1998, Pages 3581-3589

Controlling π-Facial Diastereoselectivity in the 1,3-Dipolar Cycloadditions of Diazomethane to Chiral Pentenoates and Furanones: Enantioselective Stereodivergent Syntheses of Cyclopropane Hydroxy Acids and Didehydro Amino Acids

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EID: 0038613987     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo972219a     Document Type: Article
Times cited : (29)

References (45)
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    • See, for instance: (a) Sakamura, S.; Ichichara, A.; Shiraishi, K.; Sato, H.; Nishiyama, K.; Sakai, R.; Furusaki, A.; Matsumoto, T. J. Am. Chem. Soc. 1977, 99, 636. (b) Huffman, N. E.; Yang, S. F.; Ichihara, A.; Sakamura, S. Plant Physiol. 1982, 70, 195. (c) Mitchell, R. E. Phytochemistry 1985, 24, 1485. (d) Pirrung, M. C.; McGeehan, G. M. J. Org. Chem. 1986, 51, 2103.
    • (1982) Plant Physiol. , vol.70 , pp. 195
    • Huffman, N.E.1    Yang, S.F.2    Ichihara, A.3    Sakamura, S.4
  • 3
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    • See, for instance: (a) Sakamura, S.; Ichichara, A.; Shiraishi, K.; Sato, H.; Nishiyama, K.; Sakai, R.; Furusaki, A.; Matsumoto, T. J. Am. Chem. Soc. 1977, 99, 636. (b) Huffman, N. E.; Yang, S. F.; Ichihara, A.; Sakamura, S. Plant Physiol. 1982, 70, 195. (c) Mitchell, R. E. Phytochemistry 1985, 24, 1485. (d) Pirrung, M. C.; McGeehan, G. M. J. Org. Chem. 1986, 51, 2103.
    • (1985) Phytochemistry , vol.24 , pp. 1485
    • Mitchell, R.E.1
  • 4
    • 0001265024 scopus 로고
    • See, for instance: (a) Sakamura, S.; Ichichara, A.; Shiraishi, K.; Sato, H.; Nishiyama, K.; Sakai, R.; Furusaki, A.; Matsumoto, T. J. Am. Chem. Soc. 1977, 99, 636. (b) Huffman, N. E.; Yang, S. F.; Ichihara, A.; Sakamura, S. Plant Physiol. 1982, 70, 195. (c) Mitchell, R. E. Phytochemistry 1985, 24, 1485. (d) Pirrung, M. C.; McGeehan, G. M. J. Org. Chem. 1986, 51, 2103.
    • (1986) J. Org. Chem. , vol.51 , pp. 2103
    • Pirrung, M.C.1    McGeehan, G.M.2
  • 6
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    • For reviews on the isolation, synthesis, and biological properties of cyclopropane amino acids, see: (a) Stammer, C. H. Tetrahedron 1990, 46, 2234. (b) Alami, A.; Calmes, M.; Daunis, J. Jacquier, R. Bull. Soc. Chim. Fr. 1993, 130, 5.
    • (1990) Tetrahedron , vol.46 , pp. 2234
    • Stammer, C.H.1
  • 7
    • 0001777156 scopus 로고
    • For reviews on the isolation, synthesis, and biological properties of cyclopropane amino acids, see: (a) Stammer, C. H. Tetrahedron 1990, 46, 2234. (b) Alami, A.; Calmes, M.; Daunis, J. Jacquier, R. Bull. Soc. Chim. Fr. 1993, 130, 5.
    • (1993) Bull. Soc. Chim. Fr. , vol.130 , pp. 5
    • Alami, A.1    Calmes, M.2    Daunis, J.3    Jacquier, R.4
  • 8
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    • See p 3650 and references therein
    • Kotha, S. Tetrahedron 1994, 50, 3639. See p 3650 and references therein.
    • (1994) Tetrahedron , vol.50 , pp. 3639
    • Kotha, S.1
  • 12
    • 0030970445 scopus 로고    scopus 로고
    • (b) Lee, M. G.; Du, J. F.; Chun, M. W.; Chu, C. K. J. Org. Chem. 1997, 62, 1991. These authors synthesized enantiomeric nacleosides using D- and L-glyceraldehyde as chiral precursors which, in turn, were obtained from D-mannitol and L-gulono-γ-lactone, respectively.
    • (1997) J. Org. Chem. , vol.62 , pp. 1991
    • Lee, M.G.1    Du, J.F.2    Chun, M.W.3    Chu, C.K.4
  • 13
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    • and references therein
    • Mann, J.; Partlett, N. K.; Thomas, A. J. Chem. Res. (S) 1987, 369, and references therein. Although D-glyceraldehyde acetonide is commercially available it can be easily prepared from D-mannitol according to this work.
    • (1987) J. Chem. Res. (S) , pp. 369
    • Mann, J.1    Partlett, N.K.2    Thomas, A.3
  • 19
    • 0000905924 scopus 로고
    • Hanessian, S.; Murray, P. J. Tetrahedron 1987, 43, 5055. Pyrazoline 7 is depicted in this work with anti stereochemistry, but this configuration is not justified. Although we have used polar solvents to determine specific rotation for 7 due to the low solubility of this crystalline compound in carbon tetrachloride, the latter was the solvent used by those authors.
    • (1987) Tetrahedron , vol.43 , pp. 5055
    • Hanessian, S.1    Murray, P.J.2
  • 34
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    • note
    • The atomic coordinates and thermal parameters for structure 17a are available on request from the Director of the Cambridge Crystallographic Data Centre. Any request should be accompanied by a full literature citation for this paper. Please note that the crystallographic numbering differs from that used in this article.
  • 35
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    • John Wiley and Sons: New York, and reference therein
    • March J. Advanced Organic Chemistry; John Wiley and Sons: New York 1992, p 1046 and reference therein.
    • (1992) Advanced Organic Chemistry , pp. 1046
    • March, J.1


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