Isoxazolinium salts in asymmetric synthesis. 1. Stereoselective reduction induced by a 3′-alkoxy stereocentre. A new approach to polyfunctionalized β-amino acids

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

Volumn 59, Issue 4, 2004, Pages 451-467

  Henneböhle, Marco ^a   Le Roy, Pierre Yves ^a   Hein, Matthias ^a   Ehrler, Rudolf ^a   Jäger, Volker ^a  

^a UNIVERSITY OF STUTTGART   (Germany)

Author keywords

Diastereoselective Reduction; Homoserine; Isoxazolinium Salts; Methylamino Alcohols; Amino acids

Indexed keywords

AMINO ACIDS; HYDROGENATION; SALTS;

ASYMMETRIC SYNTHESIS; CATALYTIC HYDROGENATION; DIASTEREO-SELECTIVITY; DIASTEREOMERIC RATIOS; DIASTEREOSELECTIVE REDUCTION; HOMOSERINE; N-METHYLAMINO ACID; STEREOSELECTIVE REDUCTION;

STEREOSELECTIVITY;

4,5 CYCLOHEXYLIDENEDIOXY 3 METHYLAMINOPENTANOIC ACID; ALCOHOL DERIVATIVE; AMINO ACID DERIVATIVE; CHLORIDE; ISOXAZOLINE DERIVATIVE; SODIUM DERIVATIVE; UNCLASSIFIED DRUG; VALERIC ACID DERIVATIVE;

CATALYSIS; CONFERENCE PAPER; DIASTEREOISOMER; HYDROGENATION; OXIDATION; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 2442587277     PISSN: 09320776     EISSN: None     Source Type: Journal    
DOI: 10.1515/znb-2004-0414     Document Type: Conference Paper

References (130)

1. Synthesis via Isoxazolines, 25; for part 24 see M. Kleban, P. Hilgers, J. Greul, R. Kugler, J. Li, S. Picasso, P. Vogel, V. Jäger, ChemBioChem 2, 365 (2001).
2. Taken in part from: a) R. Ehrler, Dissertation, Universität Würzburg (1985); b) Matthias Hein, Dissertation, Universität Stuttgart (1996); c) P.-Y. Le Roy, Dissertation, Universität Stuttgart (1997); d) M. Henneböhle, Dissertation, Universität Stuttgart (2002).
3. Taken in part from: a) R. Ehrler, Dissertation, Universität Würzburg (1985); b) Matthias Hein, Dissertation, Universität Stuttgart (1996); c) P.-Y. Le Roy, Dissertation, Universität Stuttgart (1997); d) M. Henneböhle, Dissertation, Universität Stuttgart (2002).
4. Taken in part from: a) R. Ehrler, Dissertation, Universität Würzburg (1985); b) Matthias Hein, Dissertation, Universität Stuttgart (1996); c) P.-Y. Le Roy, Dissertation, Universität Stuttgart (1997); d) M. Henneböhle, Dissertation, Universität Stuttgart (2002).
5. Taken in part from: a) R. Ehrler, Dissertation, Universität Würzburg (1985); b) Matthias Hein, Dissertation, Universität Stuttgart (1996); c) P.-Y. Le Roy, Dissertation, Universität Stuttgart (1997); d) M. Henneböhle, Dissertation, Universität Stuttgart (2002).
6. Reviews: U. Schöllkopf, Pure Appl. Chem. 55, 1799 (1983); M. J. Jung, in G. C. Barrett (ed.): Chemistry and Biochemistry of the Amino Acids, p. 227, Chapman and Hall, London (1985); R. M. Williams, Synthesis of Optically Active α-Amino Acids, Ch. 5, p. 208, in J. E. Baldwin, P. D. Magnus (eds): Organic Chemistry Series, Vol. 7, Pergamon Press, Oxford (1989); R. O. Duthaler, Tetrahedron 50, 1539 (1994); P. Wipf, Chem. Rev. 95, 2115 (1995).
7. Reviews: U. Schöllkopf, Pure Appl. Chem. 55, 1799 (1983); M. J. Jung, in G. C. Barrett (ed.): Chemistry and Biochemistry of the Amino Acids, p. 227, Chapman and Hall, London (1985); R. M. Williams, Synthesis of Optically Active α-Amino Acids, Ch. 5, p. 208, in J. E. Baldwin, P. D. Magnus (eds): Organic Chemistry Series, Vol. 7, Pergamon Press, Oxford (1989); R. O. Duthaler, Tetrahedron 50, 1539 (1994); P. Wipf, Chem. Rev. 95, 2115 (1995).
8. Reviews: U. Schöllkopf, Pure Appl. Chem. 55, 1799 (1983); M. J. Jung, in G. C. Barrett (ed.): Chemistry and Biochemistry of the Amino Acids, p. 227, Chapman and Hall, London (1985); R. M. Williams, Synthesis of Optically Active α-Amino Acids, Ch. 5, p. 208, in J. E. Baldwin, P. D. Magnus (eds): Organic Chemistry Series, Vol. 7, Pergamon Press, Oxford (1989); R. O. Duthaler, Tetrahedron 50, 1539 (1994); P. Wipf, Chem. Rev. 95, 2115 (1995).
9. Reviews: U. Schöllkopf, Pure Appl. Chem. 55, 1799 (1983); M. J. Jung, in G. C. Barrett (ed.): Chemistry and Biochemistry of the Amino Acids, p. 227, Chapman and Hall, London (1985); R. M. Williams, Synthesis of Optically Active α-Amino Acids, Ch. 5, p. 208, in J. E. Baldwin, P. D. Magnus (eds): Organic Chemistry Series, Vol. 7, Pergamon Press, Oxford (1989); R. O. Duthaler, Tetrahedron 50, 1539 (1994); P. Wipf, Chem. Rev. 95, 2115 (1995).
10. Reviews: U. Schöllkopf, Pure Appl. Chem. 55, 1799 (1983); M. J. Jung, in G. C. Barrett (ed.): Chemistry and Biochemistry of the Amino Acids, p. 227, Chapman and Hall, London (1985); R. M. Williams, Synthesis of Optically Active α-Amino Acids, Ch. 5, p. 208, in J. E. Baldwin, P. D. Magnus (eds): Organic Chemistry Series, Vol. 7, Pergamon Press, Oxford (1989); R. O. Duthaler, Tetrahedron 50, 1539 (1994); P. Wipf, Chem. Rev. 95, 2115 (1995).
11. a-Branched a-amino acids: H. Heimgartner, Angew. Chem. 103, 271 (1991); Angew. Chem. Int. Ed. 30, 238 (1991); C.J. Moody, P. T. Gallagher, A. P. Light-foot, A. M. Z. Slawin, J. Org. Chem. 64, 4419 (1999), and references given therein.
12. a-Branched a-amino acids: H. Heimgartner, Angew. Chem. 103, 271 (1991); Angew. Chem. Int. Ed. 30, 238 (1991); C.J. Moody, P. T. Gallagher, A. P. Light-foot, A. M. Z. Slawin, J. Org. Chem. 64, 4419 (1999), and references given therein.
13. a-Branched a-amino acids: H. Heimgartner, Angew. Chem. 103, 271 (1991); Angew. Chem. Int. Ed. 30, 238 (1991); C.J. Moody, P. T. Gallagher, A. P. Light-foot, A. M. Z. Slawin, J. Org. Chem. 64, 4419 (1999), and references given therein.
14. β-Amino Acids: a) U. Schmidt, M. Kroner, H. Griesser, Synthesis, 832 (1989); b) E. Juaristi, D. Quintana, B. Lamatsch, D. Seebach, J. Org. Chem. 56, 2553 (1991); c) E. Juaristi (ed.): Enantioselective Synthesis of β-Amino Acids, Wiley-VCH, New York (1977); d) D. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 101, 3893 (2001); e) R. P. Cheng, S. H. Gellman, W. F. DeGrado, Chem. Rev. 101, 3219 (2001); f) A.R. Minter, A.A. Fuller, A. K. Mapp, J. Am. Chem. Soc. 125, 6846 (2003).
15. β-Amino Acids: a) U. Schmidt, M. Kroner, H. Griesser, Synthesis, 832 (1989); b) E. Juaristi, D. Quintana, B. Lamatsch, D. Seebach, J. Org. Chem. 56, 2553 (1991); c) E. Juaristi (ed.): Enantioselective Synthesis of β-Amino Acids, Wiley-VCH, New York (1977); d) D. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 101, 3893 (2001); e) R. P. Cheng, S. H. Gellman, W. F. DeGrado, Chem. Rev. 101, 3219 (2001); f) A.R. Minter, A.A. Fuller, A. K. Mapp, J. Am. Chem. Soc. 125, 6846 (2003).
16. β-Amino Acids: a) U. Schmidt, M. Kroner, H. Griesser, Synthesis, 832 (1989); b) E. Juaristi, D. Quintana, B. Lamatsch, D. Seebach, J. Org. Chem. 56, 2553 (1991); c) E. Juaristi (ed.): Enantioselective Synthesis of β-Amino Acids, Wiley-VCH, New York (1977); d) D. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 101, 3893 (2001); e) R. P. Cheng, S. H. Gellman, W. F. DeGrado, Chem. Rev. 101, 3219 (2001); f) A.R. Minter, A.A. Fuller, A. K. Mapp, J. Am. Chem. Soc. 125, 6846 (2003).
17. β-Amino Acids: a) U. Schmidt, M. Kroner, H. Griesser, Synthesis, 832 (1989); b) E. Juaristi, D. Quintana, B. Lamatsch, D. Seebach, J. Org. Chem. 56, 2553 (1991); c) E. Juaristi (ed.): Enantioselective Synthesis of β-Amino Acids, Wiley-VCH, New York (1977); d) D. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 101, 3893 (2001); e) R. P. Cheng, S. H. Gellman, W. F. DeGrado, Chem. Rev. 101, 3219 (2001); f) A.R. Minter, A.A. Fuller, A. K. Mapp, J. Am. Chem. Soc. 125, 6846 (2003).
18. β-Amino Acids: a) U. Schmidt, M. Kroner, H. Griesser, Synthesis, 832 (1989); b) E. Juaristi, D. Quintana, B. Lamatsch, D. Seebach, J. Org. Chem. 56, 2553 (1991); c) E. Juaristi (ed.): Enantioselective Synthesis of β-Amino Acids, Wiley-VCH, New York (1977); d) D. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 101, 3893 (2001); e) R. P. Cheng, S. H. Gellman, W. F. DeGrado, Chem. Rev. 101, 3219 (2001); f) A.R. Minter, A.A. Fuller, A. K. Mapp, J. Am. Chem. Soc. 125, 6846 (2003).
19. β-Amino Acids: a) U. Schmidt, M. Kroner, H. Griesser, Synthesis, 832 (1989); b) E. Juaristi, D. Quintana, B. Lamatsch, D. Seebach, J. Org. Chem. 56, 2553 (1991); c) E. Juaristi (ed.): Enantioselective Synthesis of β-Amino Acids, Wiley-VCH, New York (1977); d) D. J. Hill, M. J. Mio, R. B. Prince, T. S. Hughes, J. S. Moore, Chem. Rev. 101, 3893 (2001); e) R. P. Cheng, S. H. Gellman, W. F. DeGrado, Chem. Rev. 101, 3219 (2001); f) A.R. Minter, A.A. Fuller, A. K. Mapp, J. Am. Chem. Soc. 125, 6846 (2003).
20. Lactacystin: a) P. O'Brien, Angew. Chem. 111, 339 (1999); Angew. Chem. Int. Ed. 38, 326 (1999); b) C. E. Masse, A. J. Morgan, J. Adams, J. S. Panek, Eur. J. Org. Chem. 2513 (2000); c) T. Nagamitsu, T. Sunazuka, H. Tanaka, A. B. Smith, S. Omura, J. Am. Chem. Soc. 118, 3584 (1996).
21. Lactacystin: a) P. O'Brien, Angew. Chem. 111, 339 (1999); Angew. Chem. Int. Ed. 38, 326 (1999); b) C. E. Masse, A. J. Morgan, J. Adams, J. S. Panek, Eur. J. Org. Chem. 2513 (2000); c) T. Nagamitsu, T. Sunazuka, H. Tanaka, A. B. Smith, S. Omura, J. Am. Chem. Soc. 118, 3584 (1996).
22. Lactacystin: a) P. O'Brien, Angew. Chem. 111, 339 (1999); Angew. Chem. Int. Ed. 38, 326 (1999); b) C. E. Masse, A. J. Morgan, J. Adams, J. S. Panek, Eur. J. Org. Chem. 2513 (2000); c) T. Nagamitsu, T. Sunazuka, H. Tanaka, A. B. Smith, S. Omura, J. Am. Chem. Soc. 118, 3584 (1996).
23. Lactacystin: a) P. O'Brien, Angew. Chem. 111, 339 (1999); Angew. Chem. Int. Ed. 38, 326 (1999); b) C. E. Masse, A. J. Morgan, J. Adams, J. S. Panek, Eur. J. Org. Chem. 2513 (2000); c) T. Nagamitsu, T. Sunazuka, H. Tanaka, A. B. Smith, S. Omura, J. Am. Chem. Soc. 118, 3584 (1996).
24. Cf. Myriocin: T. Fujita, K. Inone, S. Yamamoto, T. Ikumoto, S. Sasaki, J. Antibiot. 47, 216 (1994).
25. D. Enders, U. Reinhold, Tetrahedron: Asymmetry 8, 1895 (1997); R. Bloch, Chem. Rev. 98, 1407 (1998); N. Risch, M. Arend in G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann (eds): Methods of Organic Chemistry (Houben-Weyl- Müller), 4th ed., Vol. E21b, p. 1833, Thieme, Stuttgart (1995).
26. D. Enders, U. Reinhold, Tetrahedron: Asymmetry 8, 1895 (1997); R. Bloch, Chem. Rev. 98, 1407 (1998); N. Risch, M. Arend in G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann (eds): Methods of Organic Chemistry (Houben-Weyl- Müller), 4th ed., Vol. E21b, p. 1833, Thieme, Stuttgart (1995).
27. D. Enders, U. Reinhold, Tetrahedron: Asymmetry 8, 1895 (1997); R. Bloch, Chem. Rev. 98, 1407 (1998); N. Risch, M. Arend in G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann (eds): Methods of Organic Chemistry (Houben-Weyl- Müller), 4th ed., Vol. E21b, p. 1833, Thieme, Stuttgart (1995).
28. a) V. Jäger, H. Grund, V. Buß, W. Schwab, I. Müller, R. Schohe, R. Franz, R. Ehrler, Bull. Soc. Chim. Belg. 92, 1039 (1983);
29. b) V. Jäger, I. Müller, R. Schohe, M. Frey, R. Ehrler, B. Häfele, D. Schröter, Lect. Heterocycl. Chem. 8, 79 (1985);
30. c) V. Jäger, R. Franz, W. Schwab, B. Häfele, D. Schröter, D. Schäfer, W. Hümmer, E. Guntrum, B. Seidel, Studies in Organic Chemistry, Vol. 35 in J. Kovác, P. Zálupsky (eds): Chemistry of Heterocyclic Compounds, p. 58, Elsevier, Amsterdam (1988);
31. d) V. Jäger, R. Müller, T. Leibold, M. Hein, M. Schwarz, M. Fengler, L. Jaroskova, M. Pätzel, P.-Y. Le Roy, Bull. Soc. Chim. Belg. 103, 491 (1994);
32. e) P. Colinas, V. Jäger, Nitrile Oxides, in A. Padwa, W. H. Pearson (eds): Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Towards Heterocycles and Natural Products, Vol. 59, p. 361, Wiley, London, New York (2002).
33. See also: a) C. Grundmann, P. Grünanger, The Nitrile Oxides, Springer Verlag, Berlin (1977); b) A. P. Kozikowski, Ace. Chem. Res. 17, 410 (1984); c) S. A. Lang (Jr.), Y-I. Lin, Isoxazoles and their Benzo Derivatives, in A. R. Katritzky, C. W. Rees (eds): Comprehensive Heterocyclic Chemistry, Vol. 6, Pergamon Press, Oxford (1984); d) D. P. Curran, Adv. Cycloadd. 1, 129 (1988); e) K. B. G. Torssell, Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; Novel Strategies in Synthesis, VCH, Weinheim (1988); f) P. Caramella, P. Grünanger, Nitrile Oxides and Imines, in A. Padwa (ed.): 1,3-Dipolar Cycloaddition Chemistry, Vol. 1, p. 291, Wiley, New York (1988); g) S. Kanemasa, O. Tsuge, Heterocycles 30, 719 (1990); h) P. Grünanger, P. Vita-Finzi, Isoxazoles, in E. C. Taylor, A. Weissberger (ed.): The Chemistry of Heterocyclic Compounds, Vol. 49, Part. 1, p. 417, Wiley, Toronto (1991); i) S. Shatzmiller, 2-Isoxazolines, in H. Suchitzky (ed.): Progress in Heterocyclic Chemistry, Vol. 4, Pergamon Press, Oxford (1992); j) D. Sutharchana, R. Murugan, Isoxazoles, in A. R. Katritzky, C. W. Rees, E. F. V. Scriven (eds): Comprehensive Heterocyclic Chemistry II, Vol. 3, S. 222, Pergamon Press, Oxford (1996).
34. See also: a) C. Grundmann, P. Grünanger, The Nitrile Oxides, Springer Verlag, Berlin (1977); b) A. P. Kozikowski, Ace. Chem. Res. 17, 410 (1984); c) S. A. Lang (Jr.), Y-I. Lin, Isoxazoles and their Benzo Derivatives, in A. R. Katritzky, C. W. Rees (eds): Comprehensive Heterocyclic Chemistry, Vol. 6, Pergamon Press, Oxford (1984); d) D. P. Curran, Adv. Cycloadd. 1, 129 (1988); e) K. B. G. Torssell, Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; Novel Strategies in Synthesis, VCH, Weinheim (1988); f) P. Caramella, P. Grünanger, Nitrile Oxides and Imines, in A. Padwa (ed.): 1,3-Dipolar Cycloaddition Chemistry, Vol. 1, p. 291, Wiley, New York (1988); g) S. Kanemasa, O. Tsuge, Heterocycles 30, 719 (1990); h) P. Grünanger, P. Vita-Finzi, Isoxazoles, in E. C. Taylor, A. Weissberger (ed.): The Chemistry of Heterocyclic Compounds, Vol. 49, Part. 1, p. 417, Wiley, Toronto (1991); i) S. Shatzmiller, 2-Isoxazolines, in H. Suchitzky (ed.): Progress in Heterocyclic Chemistry, Vol. 4, Pergamon Press, Oxford (1992); j) D. Sutharchana, R. Murugan, Isoxazoles, in A. R. Katritzky, C. W. Rees, E. F. V. Scriven (eds): Comprehensive Heterocyclic Chemistry II, Vol. 3, S. 222, Pergamon Press, Oxford (1996).
35. See also: a) C. Grundmann, P. Grünanger, The Nitrile Oxides, Springer Verlag, Berlin (1977); b) A. P. Kozikowski, Ace. Chem. Res. 17, 410 (1984); c) S. A. Lang (Jr.), Y-I. Lin, Isoxazoles and their Benzo Derivatives, in A. R. Katritzky, C. W. Rees (eds): Comprehensive Heterocyclic Chemistry, Vol. 6, Pergamon Press, Oxford (1984); d) D. P. Curran, Adv. Cycloadd. 1, 129 (1988); e) K. B. G. Torssell, Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; Novel Strategies in Synthesis, VCH, Weinheim (1988); f) P. Caramella, P. Grünanger, Nitrile Oxides and Imines, in A. Padwa (ed.): 1,3-Dipolar Cycloaddition Chemistry, Vol. 1, p. 291, Wiley, New York (1988); g) S. Kanemasa, O. Tsuge, Heterocycles 30, 719 (1990); h) P. Grünanger, P. Vita-Finzi, Isoxazoles, in E. C. Taylor, A. Weissberger (ed.): The Chemistry of Heterocyclic Compounds, Vol. 49, Part. 1, p. 417, Wiley, Toronto (1991); i) S. Shatzmiller, 2-Isoxazolines, in H. Suchitzky (ed.): Progress in Heterocyclic Chemistry, Vol. 4, Pergamon Press, Oxford (1992); j) D. Sutharchana, R. Murugan, Isoxazoles, in A. R. Katritzky, C. W. Rees, E. F. V. Scriven (eds): Comprehensive Heterocyclic Chemistry II, Vol. 3, S. 222, Pergamon Press, Oxford (1996).
36. See also: a) C. Grundmann, P. Grünanger, The Nitrile Oxides, Springer Verlag, Berlin (1977); b) A. P. Kozikowski, Ace. Chem. Res. 17, 410 (1984); c) S. A. Lang (Jr.), Y-I. Lin, Isoxazoles and their Benzo Derivatives, in A. R. Katritzky, C. W. Rees (eds): Comprehensive Heterocyclic Chemistry, Vol. 6, Pergamon Press, Oxford (1984); d) D. P. Curran, Adv. Cycloadd. 1, 129 (1988); e) K. B. G. Torssell, Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; Novel Strategies in Synthesis, VCH, Weinheim (1988); f) P. Caramella, P. Grünanger, Nitrile Oxides and Imines, in A. Padwa (ed.): 1,3-Dipolar Cycloaddition Chemistry, Vol. 1, p. 291, Wiley, New York (1988); g) S. Kanemasa, O. Tsuge, Heterocycles 30, 719 (1990); h) P. Grünanger, P. Vita-Finzi, Isoxazoles, in E. C. Taylor, A. Weissberger (ed.): The Chemistry of Heterocyclic Compounds, Vol. 49, Part. 1, p. 417, Wiley, Toronto (1991); i) S. Shatzmiller, 2-Isoxazolines, in H. Suchitzky (ed.): Progress in Heterocyclic Chemistry, Vol. 4, Pergamon Press, Oxford (1992); j) D. Sutharchana, R. Murugan, Isoxazoles, in A. R. Katritzky, C. W. Rees, E. F. V. Scriven (eds): Comprehensive Heterocyclic Chemistry II, Vol. 3, S. 222, Pergamon Press, Oxford (1996).
37. See also: a) C. Grundmann, P. Grünanger, The Nitrile Oxides, Springer Verlag, Berlin (1977); b) A. P. Kozikowski, Ace. Chem. Res. 17, 410 (1984); c) S. A. Lang (Jr.), Y-I. Lin, Isoxazoles and their Benzo Derivatives, in A. R. Katritzky, C. W. Rees (eds): Comprehensive Heterocyclic Chemistry, Vol. 6, Pergamon Press, Oxford (1984); d) D. P. Curran, Adv. Cycloadd. 1, 129 (1988); e) K. B. G. Torssell, Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; Novel Strategies in Synthesis, VCH, Weinheim (1988); f) P. Caramella, P. Grünanger, Nitrile Oxides and Imines, in A. Padwa (ed.): 1,3-Dipolar Cycloaddition Chemistry, Vol. 1, p. 291, Wiley, New York (1988); g) S. Kanemasa, O. Tsuge, Heterocycles 30, 719 (1990); h) P. Grünanger, P. Vita-Finzi, Isoxazoles, in E. C. Taylor, A. Weissberger (ed.): The Chemistry of Heterocyclic Compounds, Vol. 49, Part. 1, p. 417, Wiley, Toronto (1991); i) S. Shatzmiller, 2-Isoxazolines, in H. Suchitzky (ed.): Progress in Heterocyclic Chemistry, Vol. 4, Pergamon Press, Oxford (1992); j) D. Sutharchana, R. Murugan, Isoxazoles, in A. R. Katritzky, C. W. Rees, E. F. V. Scriven (eds): Comprehensive Heterocyclic Chemistry II, Vol. 3, S. 222, Pergamon Press, Oxford (1996).
38. See also: a) C. Grundmann, P. Grünanger, The Nitrile Oxides, Springer Verlag, Berlin (1977); b) A. P. Kozikowski, Ace. Chem. Res. 17, 410 (1984); c) S. A. Lang (Jr.), Y-I. Lin, Isoxazoles and their Benzo Derivatives, in A. R. Katritzky, C. W. Rees (eds): Comprehensive Heterocyclic Chemistry, Vol. 6, Pergamon Press, Oxford (1984); d) D. P. Curran, Adv. Cycloadd. 1, 129 (1988); e) K. B. G. Torssell, Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; Novel Strategies in Synthesis, VCH, Weinheim (1988); f) P. Caramella, P. Grünanger, Nitrile Oxides and Imines, in A. Padwa (ed.): 1,3-Dipolar Cycloaddition Chemistry, Vol. 1, p. 291, Wiley, New York (1988); g) S. Kanemasa, O. Tsuge, Heterocycles 30, 719 (1990); h) P. Grünanger, P. Vita-Finzi, Isoxazoles, in E. C. Taylor, A. Weissberger (ed.): The Chemistry of Heterocyclic Compounds, Vol. 49, Part. 1, p. 417, Wiley, Toronto (1991); i) S. Shatzmiller, 2-Isoxazolines, in H. Suchitzky (ed.): Progress in Heterocyclic Chemistry, Vol. 4, Pergamon Press, Oxford (1992); j) D. Sutharchana, R. Murugan, Isoxazoles, in A. R. Katritzky, C. W. Rees, E. F. V. Scriven (eds): Comprehensive Heterocyclic Chemistry II, Vol. 3, S. 222, Pergamon Press, Oxford (1996).
39. See also: a) C. Grundmann, P. Grünanger, The Nitrile Oxides, Springer Verlag, Berlin (1977); b) A. P. Kozikowski, Ace. Chem. Res. 17, 410 (1984); c) S. A. Lang (Jr.), Y-I. Lin, Isoxazoles and their Benzo Derivatives, in A. R. Katritzky, C. W. Rees (eds): Comprehensive Heterocyclic Chemistry, Vol. 6, Pergamon Press, Oxford (1984); d) D. P. Curran, Adv. Cycloadd. 1, 129 (1988); e) K. B. G. Torssell, Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; Novel Strategies in Synthesis, VCH, Weinheim (1988); f) P. Caramella, P. Grünanger, Nitrile Oxides and Imines, in A. Padwa (ed.): 1,3-Dipolar Cycloaddition Chemistry, Vol. 1, p. 291, Wiley, New York (1988); g) S. Kanemasa, O. Tsuge, Heterocycles 30, 719 (1990); h) P. Grünanger, P. Vita-Finzi, Isoxazoles, in E. C. Taylor, A. Weissberger (ed.): The Chemistry of Heterocyclic Compounds, Vol. 49, Part. 1, p. 417, Wiley, Toronto (1991); i) S. Shatzmiller, 2-Isoxazolines, in H. Suchitzky (ed.): Progress in Heterocyclic Chemistry, Vol. 4, Pergamon Press, Oxford (1992); j) D. Sutharchana, R. Murugan, Isoxazoles, in A. R. Katritzky, C. W. Rees, E. F. V. Scriven (eds): Comprehensive Heterocyclic Chemistry II, Vol. 3, S. 222, Pergamon Press, Oxford (1996).
40. See also: a) C. Grundmann, P. Grünanger, The Nitrile Oxides, Springer Verlag, Berlin (1977); b) A. P. Kozikowski, Ace. Chem. Res. 17, 410 (1984); c) S. A. Lang (Jr.), Y-I. Lin, Isoxazoles and their Benzo Derivatives, in A. R. Katritzky, C. W. Rees (eds): Comprehensive Heterocyclic Chemistry, Vol. 6, Pergamon Press, Oxford (1984); d) D. P. Curran, Adv. Cycloadd. 1, 129 (1988); e) K. B. G. Torssell, Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; Novel Strategies in Synthesis, VCH, Weinheim (1988); f) P. Caramella, P. Grünanger, Nitrile Oxides and Imines, in A. Padwa (ed.): 1,3-Dipolar Cycloaddition Chemistry, Vol. 1, p. 291, Wiley, New York (1988); g) S. Kanemasa, O. Tsuge, Heterocycles 30, 719 (1990); h) P. Grünanger, P. Vita-Finzi, Isoxazoles, in E. C. Taylor, A. Weissberger (ed.): The Chemistry of Heterocyclic Compounds, Vol. 49, Part. 1, p. 417, Wiley, Toronto (1991); i) S. Shatzmiller, 2-Isoxazolines, in H. Suchitzky (ed.): Progress in Heterocyclic Chemistry, Vol. 4, Pergamon Press, Oxford (1992); j) D. Sutharchana, R. Murugan, Isoxazoles, in A. R. Katritzky, C. W. Rees, E. F. V. Scriven (eds): Comprehensive Heterocyclic Chemistry II, Vol. 3, S. 222, Pergamon Press, Oxford (1996).
41. See also: a) C. Grundmann, P. Grünanger, The Nitrile Oxides, Springer Verlag, Berlin (1977); b) A. P. Kozikowski, Ace. Chem. Res. 17, 410 (1984); c) S. A. Lang (Jr.), Y-I. Lin, Isoxazoles and their Benzo Derivatives, in A. R. Katritzky, C. W. Rees (eds): Comprehensive Heterocyclic Chemistry, Vol. 6, Pergamon Press, Oxford (1984); d) D. P. Curran, Adv. Cycloadd. 1, 129 (1988); e) K. B. G. Torssell, Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; Novel Strategies in Synthesis, VCH, Weinheim (1988); f) P. Caramella, P. Grünanger, Nitrile Oxides and Imines, in A. Padwa (ed.): 1,3-Dipolar Cycloaddition Chemistry, Vol. 1, p. 291, Wiley, New York (1988); g) S. Kanemasa, O. Tsuge, Heterocycles 30, 719 (1990); h) P. Grünanger, P. Vita-Finzi, Isoxazoles, in E. C. Taylor, A. Weissberger (ed.): The Chemistry of Heterocyclic Compounds, Vol. 49, Part. 1, p. 417, Wiley, Toronto (1991); i) S. Shatzmiller, 2-Isoxazolines, in H. Suchitzky (ed.): Progress in Heterocyclic Chemistry, Vol. 4, Pergamon Press, Oxford (1992); j) D. Sutharchana, R. Murugan, Isoxazoles, in A. R. Katritzky, C. W. Rees, E. F. V. Scriven (eds): Comprehensive Heterocyclic Chemistry II, Vol. 3, S. 222, Pergamon Press, Oxford (1996).
42. See also: a) C. Grundmann, P. Grünanger, The Nitrile Oxides, Springer Verlag, Berlin (1977); b) A. P. Kozikowski, Ace. Chem. Res. 17, 410 (1984); c) S. A. Lang (Jr.), Y-I. Lin, Isoxazoles and their Benzo Derivatives, in A. R. Katritzky, C. W. Rees (eds): Comprehensive Heterocyclic Chemistry, Vol. 6, Pergamon Press, Oxford (1984); d) D. P. Curran, Adv. Cycloadd. 1, 129 (1988); e) K. B. G. Torssell, Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis; Novel Strategies in Synthesis, VCH, Weinheim (1988); f) P. Caramella, P. Grünanger, Nitrile Oxides and Imines, in A. Padwa (ed.): 1,3-Dipolar Cycloaddition Chemistry, Vol. 1, p. 291, Wiley, New York (1988); g) S. Kanemasa, O. Tsuge, Heterocycles 30, 719 (1990); h) P. Grünanger, P. Vita-Finzi, Isoxazoles, in E. C. Taylor, A. Weissberger (ed.): The Chemistry of Heterocyclic Compounds, Vol. 49, Part. 1, p. 417, Wiley, Toronto (1991); i) S. Shatzmiller, 2-Isoxazolines, in H. Suchitzky (ed.): Progress in Heterocyclic Chemistry, Vol. 4, Pergamon Press, Oxford (1992); j) D. Sutharchana, R. Murugan, Isoxazoles, in A. R. Katritzky, C. W. Rees, E. F. V. Scriven (eds): Comprehensive Heterocyclic Chemistry II, Vol. 3, S. 222, Pergamon Press, Oxford (1996).
43. T. Franz, M. Hein, U. Veith, V. Jäger, K. Peters, H. G. von Schnering, Angew. Chem. 106, 1308 (1994); Angew. Chem. Int. Ed. 33, 1298 (1994); N. Meunier, U. Veith, V. Jäger, J. Chem. Soc., Chem. Commun. 331 (1996); U. Veith, O. Schwardt, V. Jäger, Synlett, 1181 (1996).
44. T. Franz, M. Hein, U. Veith, V. Jäger, K. Peters, H. G. von Schnering, Angew. Chem. 106, 1308 (1994); Angew. Chem. Int. Ed. 33, 1298 (1994); N. Meunier, U. Veith, V. Jäger, J. Chem. Soc., Chem. Commun. 331 (1996); U. Veith, O. Schwardt, V. Jäger, Synlett, 1181 (1996).
45. T. Franz, M. Hein, U. Veith, V. Jäger, K. Peters, H. G. von Schnering, Angew. Chem. 106, 1308 (1994); Angew. Chem. Int. Ed. 33, 1298 (1994); N. Meunier, U. Veith, V. Jäger, J. Chem. Soc., Chem. Commun. 331 (1996); U. Veith, O. Schwardt, V. Jäger, Synlett, 1181 (1996).
46. T. Franz, M. Hein, U. Veith, V. Jäger, K. Peters, H. G. von Schnering, Angew. Chem. 106, 1308 (1994); Angew. Chem. Int. Ed. 33, 1298 (1994); N. Meunier, U. Veith, V. Jäger, J. Chem. Soc., Chem. Commun. 331 (1996); U. Veith, O. Schwardt, V. Jäger, Synlett, 1181 (1996).
47. See also: K. Weinges, H. Blackholm, Chem. Ber. 113, 3098 (1980); H. Kunz, D. Schazenbach, Angew. Chem. 101, 1042 (1989); Angew. Chem. Int. Ed. 28, 1068 (1989); C. Cativiela, M. D. Diaz-de-Villegas, J. A. Gálvez, Tetrahedron: Asymmetry 5, 261 (1994).
48. See also: K. Weinges, H. Blackholm, Chem. Ber. 113, 3098 (1980); H. Kunz, D. Schazenbach, Angew. Chem. 101, 1042 (1989); Angew. Chem. Int. Ed. 28, 1068 (1989); C. Cativiela, M. D. Diaz-de-Villegas, J. A. Gálvez, Tetrahedron: Asymmetry 5, 261 (1994).
49. See also: K. Weinges, H. Blackholm, Chem. Ber. 113, 3098 (1980); H. Kunz, D. Schazenbach, Angew. Chem. 101, 1042 (1989); Angew. Chem. Int. Ed. 28, 1068 (1989); C. Cativiela, M. D. Diaz-de-Villegas, J. A. Gálvez, Tetrahedron: Asymmetry 5, 261 (1994).
50. See also: K. Weinges, H. Blackholm, Chem. Ber. 113, 3098 (1980); H. Kunz, D. Schazenbach, Angew. Chem. 101, 1042 (1989); Angew. Chem. Int. Ed. 28, 1068 (1989); C. Cativiela, M. D. Diaz-de-Villegas, J. A. Gálvez, Tetrahedron: Asymmetry 5, 261 (1994).
51. V. Jäger, L. Bierer, H.-Q. Dong, A. M. Palmer, D. Shaw, W. Frey, J. Heterocyclic Chem. 37, 455 (2000).
52. A. M. Palmer, V. Jäger, Eur. J. Org. Chem. 1293 (2001).
53. V. Jäger, R. Öhrlein, V. Wehner, H. Griesser, A. Menzel, Synthesis, 1691 (1999); V. Jäger, R. Öhrlein, V. Wehner, P. Poggendorf, B. Steuer, J. Raczko, H. Griesser, F.-M. Kieß, A. Menzel, Enantiomer 4, 205 (1999).
54. V. Jäger, R. Öhrlein, V. Wehner, H. Griesser, A. Menzel, Synthesis, 1691 (1999); V. Jäger, R. Öhrlein, V. Wehner, P. Poggendorf, B. Steuer, J. Raczko, H. Griesser, F.-M. Kieß, A. Menzel, Enantiomer 4, 205 (1999).
55. B. Häfele, D. Schröter, V. Jäger, Angew. Chem. 98, 89 (1986); Angew. Chem. Int. Ed. 25, 87 (1986); V. Jäger, W. Hümmer, Angew. Chem. 102, 1182 (1990); Angew. Chem. Int. Ed. 29, 1171 (1990); B. Kirschbaum, U. Stahl, V. Jäger, Bull. Soc. Chim. Belg. 103, 425 (1994); V. Jäger, T. Gracza, E. Dubois, T. Hasenöhrl, W. Hümmer, U. Kautz, B. Kirschbaum, A. Lieberknecht, L. Remen, D. Shaw, U. Stahl, O. Stephan, Organic Synthesis via Organometallics (OSM 5), p. 331, in G. Helmchen (ed.): Proceedings of the Fifth Symposium, Heidelberg, Sep 26-28 (1996), F. Vieweg & Sohn Verlagsges., Braunschweig/Wiesbaden (1997); A. Palmer, V. Jäger, Synlett 10, 1405 (2000).
56. B. Häfele, D. Schröter, V. Jäger, Angew. Chem. 98, 89 (1986); Angew. Chem. Int. Ed. 25, 87 (1986); V. Jäger, W. Hümmer, Angew. Chem. 102, 1182 (1990); Angew. Chem. Int. Ed. 29, 1171 (1990); B. Kirschbaum, U. Stahl, V. Jäger, Bull. Soc. Chim. Belg. 103, 425 (1994); V. Jäger, T. Gracza, E. Dubois, T. Hasenöhrl, W. Hümmer, U. Kautz, B. Kirschbaum, A. Lieberknecht, L. Remen, D. Shaw, U. Stahl, O. Stephan, Organic Synthesis via Organometallics (OSM 5), p. 331, in G. Helmchen (ed.): Proceedings of the Fifth Symposium, Heidelberg, Sep 26-28 (1996), F. Vieweg & Sohn Verlagsges., Braunschweig/Wiesbaden (1997); A. Palmer, V. Jäger, Synlett 10, 1405 (2000).
57. B. Häfele, D. Schröter, V. Jäger, Angew. Chem. 98, 89 (1986); Angew. Chem. Int. Ed. 25, 87 (1986); V. Jäger, W. Hümmer, Angew. Chem. 102, 1182 (1990); Angew. Chem. Int. Ed. 29, 1171 (1990); B. Kirschbaum, U. Stahl, V. Jäger, Bull. Soc. Chim. Belg. 103, 425 (1994); V. Jäger, T. Gracza, E. Dubois, T. Hasenöhrl, W. Hümmer, U. Kautz, B. Kirschbaum, A. Lieberknecht, L. Remen, D. Shaw, U. Stahl, O. Stephan, Organic Synthesis via Organometallics (OSM 5), p. 331, in G. Helmchen (ed.): Proceedings of the Fifth Symposium, Heidelberg, Sep 26-28 (1996), F. Vieweg & Sohn Verlagsges., Braunschweig/Wiesbaden (1997); A. Palmer, V. Jäger, Synlett 10, 1405 (2000).
58. B. Häfele, D. Schröter, V. Jäger, Angew. Chem. 98, 89 (1986); Angew. Chem. Int. Ed. 25, 87 (1986); V. Jäger, W. Hümmer, Angew. Chem. 102, 1182 (1990); Angew. Chem. Int. Ed. 29, 1171 (1990); B. Kirschbaum, U. Stahl, V. Jäger, Bull. Soc. Chim. Belg. 103, 425 (1994); V. Jäger, T. Gracza, E. Dubois, T. Hasenöhrl, W. Hümmer, U. Kautz, B. Kirschbaum, A. Lieberknecht, L. Remen, D. Shaw, U. Stahl, O. Stephan, Organic Synthesis via Organometallics (OSM 5), p. 331, in G. Helmchen (ed.): Proceedings of the Fifth Symposium, Heidelberg, Sep 26-28 (1996), F. Vieweg & Sohn Verlagsges., Braunschweig/Wiesbaden (1997); A. Palmer, V. Jäger, Synlett 10, 1405 (2000).
59. B. Häfele, D. Schröter, V. Jäger, Angew. Chem. 98, 89 (1986); Angew. Chem. Int. Ed. 25, 87 (1986); V. Jäger, W. Hümmer, Angew. Chem. 102, 1182 (1990); Angew. Chem. Int. Ed. 29, 1171 (1990); B. Kirschbaum, U. Stahl, V. Jäger, Bull. Soc. Chim. Belg. 103, 425 (1994); V. Jäger, T. Gracza, E. Dubois, T. Hasenöhrl, W. Hümmer, U. Kautz, B. Kirschbaum, A. Lieberknecht, L. Remen, D. Shaw, U. Stahl, O. Stephan, Organic Synthesis via Organometallics (OSM 5), p. 331, in G. Helmchen (ed.): Proceedings of the Fifth Symposium, Heidelberg, Sep 26-28 (1996), F. Vieweg & Sohn Verlagsges., Braunschweig/Wiesbaden (1997); A. Palmer, V. Jäger, Synlett 10, 1405 (2000).
60. B. Häfele, D. Schröter, V. Jäger, Angew. Chem. 98, 89 (1986); Angew. Chem. Int. Ed. 25, 87 (1986); V. Jäger, W. Hümmer, Angew. Chem. 102, 1182 (1990); Angew. Chem. Int. Ed. 29, 1171 (1990); B. Kirschbaum, U. Stahl, V. Jäger, Bull. Soc. Chim. Belg. 103, 425 (1994); V. Jäger, T. Gracza, E. Dubois, T. Hasenöhrl, W. Hümmer, U. Kautz, B. Kirschbaum, A. Lieberknecht, L. Remen, D. Shaw, U. Stahl, O. Stephan, Organic Synthesis via Organometallics (OSM 5), p. 331, in G. Helmchen (ed.): Proceedings of the Fifth Symposium, Heidelberg, Sep 26-28 (1996), F. Vieweg & Sohn Verlagsges., Braunschweig/Wiesbaden (1997); A. Palmer, V. Jäger, Synlett 10, 1405 (2000).
61. B. Häfele, D. Schröter, V. Jäger, Angew. Chem. 98, 89 (1986); Angew. Chem. Int. Ed. 25, 87 (1986); V. Jäger, W. Hümmer, Angew. Chem. 102, 1182 (1990); Angew. Chem. Int. Ed. 29, 1171 (1990); B. Kirschbaum, U. Stahl, V. Jäger, Bull. Soc. Chim. Belg. 103, 425 (1994); V. Jäger, T. Gracza, E. Dubois, T. Hasenöhrl, W. Hümmer, U. Kautz, B. Kirschbaum, A. Lieberknecht, L. Remen, D. Shaw, U. Stahl, O. Stephan, Organic Synthesis via Organometallics (OSM 5), p. 331, in G. Helmchen (ed.): Proceedings of the Fifth Symposium, Heidelberg, Sep 26-28 (1996), F. Vieweg & Sohn Verlagsges., Braunschweig/Wiesbaden (1997); A. Palmer, V. Jäger, Synlett 10, 1405 (2000).
62. a) V. Buß, Dissertation, Universität Gießen (1979);
63. b) W. Schwab, Dissertation, Universität Gießen (1978);
64. c) R. Franz, Dissertation, Universität Würzburg (1985);
65. d) R. Müller, Dissertation, Universität Würzburg (1992);
66. e) T. Leibold, Dissertation, Universität Stuttgart (1995);
67. f) R. Ehrler, Dissertation, Universität Würzburg (1986);
68. g) cf. ref. [9].
69. a) P. J. Zimmermann, Dissertation, Universität Stuttgart (2000);
70. b) P. J. Zimmermann, I. Blanarikova, V. Jäger, Angew. Chem. 112, 936 (2000); Angew. Chem. Int. Ed. 39, 910 (2000);
71. b) P. J. Zimmermann, I. Blanarikova, V. Jäger, Angew. Chem. 112, 936 (2000); Angew. Chem. Int. Ed. 39, 910 (2000);
72. c) J.-Y. Lee, Dissertation, Universität Stuttgart (planned).
73. G. Drehfahl, H. Hörhold, Chem. Ber. 97, 159 (1964); T. Kusumi, H. Kakisawa, S. Suzuki, K. Harada, C. Kashima, Bull. Chem. Soc. Jpn. 51, 1261 (1978); T. Kametani, S.-P. Huang, S. Yokohama, Y. Suzuki, M. Ihara, J. Am. Chem. Soc. 102, 2060 (1980); T. Kametani, A. Nakayama, Y. Nakayama, T. Ikuta, R. Kubo, E. Goto, T. Honda, K. Fukumoto, Heterocycles 16, 53 (1981); G. Zimmermann, W. Hass, H. Faasch, H. Schmalle, W. A. König, Liebigs Ann. Chem. 2165 (1985); W. A. König, H. Hahn, R. Rathmann, W. Hass, A. Keckeisen, H. Hagenmaier, C. Bormann, W. Dehler, R. Kurth, H. Zähner, Liebigs Ann. Chem. 407 (1986); W. Hass, W. A. König, Liebigs Ann. Chem. 1615 (1982); A. G. M. Barrett, D. Dhanak, S. A. Lebold, M. A. Russell, J. Org. Chem. 56, 1894 (1991).
74. G. Drehfahl, H. Hörhold, Chem. Ber. 97, 159 (1964); T. Kusumi, H. Kakisawa, S. Suzuki, K. Harada, C. Kashima, Bull. Chem. Soc. Jpn. 51, 1261 (1978); T. Kametani, S.-P. Huang, S. Yokohama, Y. Suzuki, M. Ihara, J. Am. Chem. Soc. 102, 2060 (1980); T. Kametani, A. Nakayama, Y. Nakayama, T. Ikuta, R. Kubo, E. Goto, T. Honda, K. Fukumoto, Heterocycles 16, 53 (1981); G. Zimmermann, W. Hass, H. Faasch, H. Schmalle, W. A. König, Liebigs Ann. Chem. 2165 (1985); W. A. König, H. Hahn, R. Rathmann, W. Hass, A. Keckeisen, H. Hagenmaier, C. Bormann, W. Dehler, R. Kurth, H. Zähner, Liebigs Ann. Chem. 407 (1986); W. Hass, W. A. König, Liebigs Ann. Chem. 1615 (1982); A. G. M. Barrett, D. Dhanak, S. A. Lebold, M. A. Russell, J. Org. Chem. 56, 1894 (1991).
75. G. Drehfahl, H. Hörhold, Chem. Ber. 97, 159 (1964); T. Kusumi, H. Kakisawa, S. Suzuki, K. Harada, C. Kashima, Bull. Chem. Soc. Jpn. 51, 1261 (1978); T. Kametani, S.-P. Huang, S. Yokohama, Y. Suzuki, M. Ihara, J. Am. Chem. Soc. 102, 2060 (1980); T. Kametani, A. Nakayama, Y. Nakayama, T. Ikuta, R. Kubo, E. Goto, T. Honda, K. Fukumoto, Heterocycles 16, 53 (1981); G. Zimmermann, W. Hass, H. Faasch, H. Schmalle, W. A. König, Liebigs Ann. Chem. 2165 (1985); W. A. König, H. Hahn, R. Rathmann, W. Hass, A. Keckeisen, H. Hagenmaier, C. Bormann, W. Dehler, R. Kurth, H. Zähner, Liebigs Ann. Chem. 407 (1986); W. Hass, W. A. König, Liebigs Ann. Chem. 1615 (1982); A. G. M. Barrett, D. Dhanak, S. A. Lebold, M. A. Russell, J. Org. Chem. 56, 1894 (1991).
76. G. Drehfahl, H. Hörhold, Chem. Ber. 97, 159 (1964); T. Kusumi, H. Kakisawa, S. Suzuki, K. Harada, C. Kashima, Bull. Chem. Soc. Jpn. 51, 1261 (1978); T. Kametani, S.-P. Huang, S. Yokohama, Y. Suzuki, M. Ihara, J. Am. Chem. Soc. 102, 2060 (1980); T. Kametani, A. Nakayama, Y. Nakayama, T. Ikuta, R. Kubo, E. Goto, T. Honda, K. Fukumoto, Heterocycles 16, 53 (1981); G. Zimmermann, W. Hass, H. Faasch, H. Schmalle, W. A. König, Liebigs Ann. Chem. 2165 (1985); W. A. König, H. Hahn, R. Rathmann, W. Hass, A. Keckeisen, H. Hagenmaier, C. Bormann, W. Dehler, R. Kurth, H. Zähner, Liebigs Ann. Chem. 407 (1986); W. Hass, W. A. König, Liebigs Ann. Chem. 1615 (1982); A. G. M. Barrett, D. Dhanak, S. A. Lebold, M. A. Russell, J. Org. Chem. 56, 1894 (1991).
77. G. Drehfahl, H. Hörhold, Chem. Ber. 97, 159 (1964); T. Kusumi, H. Kakisawa, S. Suzuki, K. Harada, C. Kashima, Bull. Chem. Soc. Jpn. 51, 1261 (1978); T. Kametani, S.-P. Huang, S. Yokohama, Y. Suzuki, M. Ihara, J. Am. Chem. Soc. 102, 2060 (1980); T. Kametani, A. Nakayama, Y. Nakayama, T. Ikuta, R. Kubo, E. Goto, T. Honda, K. Fukumoto, Heterocycles 16, 53 (1981); G. Zimmermann, W. Hass, H. Faasch, H. Schmalle, W. A. König, Liebigs Ann. Chem. 2165 (1985); W. A. König, H. Hahn, R. Rathmann, W. Hass, A. Keckeisen, H. Hagenmaier, C. Bormann, W. Dehler, R. Kurth, H. Zähner, Liebigs Ann. Chem. 407 (1986); W. Hass, W. A. König, Liebigs Ann. Chem. 1615 (1982); A. G. M. Barrett, D. Dhanak, S. A. Lebold, M. A. Russell, J. Org. Chem. 56, 1894 (1991).
78. G. Drehfahl, H. Hörhold, Chem. Ber. 97, 159 (1964); T. Kusumi, H. Kakisawa, S. Suzuki, K. Harada, C. Kashima, Bull. Chem. Soc. Jpn. 51, 1261 (1978); T. Kametani, S.-P. Huang, S. Yokohama, Y. Suzuki, M. Ihara, J. Am. Chem. Soc. 102, 2060 (1980); T. Kametani, A. Nakayama, Y. Nakayama, T. Ikuta, R. Kubo, E. Goto, T. Honda, K. Fukumoto, Heterocycles 16, 53 (1981); G. Zimmermann, W. Hass, H. Faasch, H. Schmalle, W. A. König, Liebigs Ann. Chem. 2165 (1985); W. A. König, H. Hahn, R. Rathmann, W. Hass, A. Keckeisen, H. Hagenmaier, C. Bormann, W. Dehler, R. Kurth, H. Zähner, Liebigs Ann. Chem. 407 (1986); W. Hass, W. A. König, Liebigs Ann. Chem. 1615 (1982); A. G. M. Barrett, D. Dhanak, S. A. Lebold, M. A. Russell, J. Org. Chem. 56, 1894 (1991).
79. G. Drehfahl, H. Hörhold, Chem. Ber. 97, 159 (1964); T. Kusumi, H. Kakisawa, S. Suzuki, K. Harada, C. Kashima, Bull. Chem. Soc. Jpn. 51, 1261 (1978); T. Kametani, S.-P. Huang, S. Yokohama, Y. Suzuki, M. Ihara, J. Am. Chem. Soc. 102, 2060 (1980); T. Kametani, A. Nakayama, Y. Nakayama, T. Ikuta, R. Kubo, E. Goto, T. Honda, K. Fukumoto, Heterocycles 16, 53 (1981); G. Zimmermann, W. Hass, H. Faasch, H. Schmalle, W. A. König, Liebigs Ann. Chem. 2165 (1985); W. A. König, H. Hahn, R. Rathmann, W. Hass, A. Keckeisen, H. Hagenmaier, C. Bormann, W. Dehler, R. Kurth, H. Zähner, Liebigs Ann. Chem. 407 (1986); W. Hass, W. A. König, Liebigs Ann. Chem. 1615 (1982); A. G. M. Barrett, D. Dhanak, S. A. Lebold, M. A. Russell, J. Org. Chem. 56, 1894 (1991).
80. G. Drehfahl, H. Hörhold, Chem. Ber. 97, 159 (1964); T. Kusumi, H. Kakisawa, S. Suzuki, K. Harada, C. Kashima, Bull. Chem. Soc. Jpn. 51, 1261 (1978); T. Kametani, S.-P. Huang, S. Yokohama, Y. Suzuki, M. Ihara, J. Am. Chem. Soc. 102, 2060 (1980); T. Kametani, A. Nakayama, Y. Nakayama, T. Ikuta, R. Kubo, E. Goto, T. Honda, K. Fukumoto, Heterocycles 16, 53 (1981); G. Zimmermann, W. Hass, H. Faasch, H. Schmalle, W. A. König, Liebigs Ann. Chem. 2165 (1985); W. A. König, H. Hahn, R. Rathmann, W. Hass, A. Keckeisen, H. Hagenmaier, C. Bormann, W. Dehler, R. Kurth, H. Zähner, Liebigs Ann. Chem. 407 (1986); W. Hass, W. A. König, Liebigs Ann. Chem. 1615 (1982); A. G. M. Barrett, D. Dhanak, S. A. Lebold, M. A. Russell, J. Org. Chem. 56, 1894 (1991).
81. R. Müller, T. Leibold, M. Pätzel, V. Jäger, Angew. Chem. 106, 1305 (1994); Angew. Chem. Int. Ed. 33, 1295 (1994); C. Schaller, P. Vogel, V. Jäger, Carbohydr. Res. 314, 25 (1998).
82. R. Müller, T. Leibold, M. Pätzel, V. Jäger, Angew. Chem. 106, 1305 (1994); Angew. Chem. Int. Ed. 33, 1295 (1994); C. Schaller, P. Vogel, V. Jäger, Carbohydr. Res. 314, 25 (1998).
83. R. Müller, T. Leibold, M. Pätzel, V. Jäger, Angew. Chem. 106, 1305 (1994); Angew. Chem. Int. Ed. 33, 1295 (1994); C. Schaller, P. Vogel, V. Jäger, Carbohydr. Res. 314, 25 (1998).
84. For uses of 2-furyl as carboxyl equivalent see, f. e.: a) G. Alvaro, G. Martelli, D. Savoia, A. Zoffoli, Synthesis 1773 (1988); b) see ref. [4] (Moody).
85. For uses of 2-furyl as carboxyl equivalent see, f. e.: a) G. Alvaro, G. Martelli, D. Savoia, A. Zoffoli, Synthesis 1773 (1988); b) see ref. [4] (Moody).
86. Cf. ref. [11] (synthesis of the statine family).
87. Cf. use of styryl as latent carboxyl in related oxime ether additions: ref. [4] (Moody); cf. also complementary strategy to elaborate a carboxyl group at the (former) 5-position of the isoxazoline by reduction to the diol and subsequent oxidative cleavage, ref. [5f].
88. V. Jäger, H. Grund, Angew. Chem. 88, 27 (1976); Angew. Chem. Int. Ed. 15, 50 (1976); V. Jäger, W. Schwab, Tetrahedron Lett. 3129 (1978); H. Grund, V. Jäger, Liebigs Ann. Chem. 80 (1980); V. Jäger, V. Buß, W. Schwab, Liebigs Ann. Chem. 122 (1980).
89. V. Jäger, H. Grund, Angew. Chem. 88, 27 (1976); Angew. Chem. Int. Ed. 15, 50 (1976); V. Jäger, W. Schwab, Tetrahedron Lett. 3129 (1978); H. Grund, V. Jäger, Liebigs Ann. Chem. 80 (1980); V. Jäger, V. Buß, W. Schwab, Liebigs Ann. Chem. 122 (1980).
90. V. Jäger, H. Grund, Angew. Chem. 88, 27 (1976); Angew. Chem. Int. Ed. 15, 50 (1976); V. Jäger, W. Schwab, Tetrahedron Lett. 3129 (1978); H. Grund, V. Jäger, Liebigs Ann. Chem. 80 (1980); V. Jäger, V. Buß, W. Schwab, Liebigs Ann. Chem. 122 (1980).
91. V. Jäger, H. Grund, Angew. Chem. 88, 27 (1976); Angew. Chem. Int. Ed. 15, 50 (1976); V. Jäger, W. Schwab, Tetrahedron Lett. 3129 (1978); H. Grund, V. Jäger, Liebigs Ann. Chem. 80 (1980); V. Jäger, V. Buß, W. Schwab, Liebigs Ann. Chem. 122 (1980).
92. V. Jäger, H. Grund, Angew. Chem. 88, 27 (1976); Angew. Chem. Int. Ed. 15, 50 (1976); V. Jäger, W. Schwab, Tetrahedron Lett. 3129 (1978); H. Grund, V. Jäger, Liebigs Ann. Chem. 80 (1980); V. Jäger, V. Buß, W. Schwab, Liebigs Ann. Chem. 122 (1980).
93. a) H. Uno, T. Terekawa, and H. Suzuki, Bull. Chem. Soc. Jpn. 66, 2730 (1993);
94. b) cf. rediscoveries: K. S.-L. Huang, E. H. Lee, M. M. Olmstead, M. J. Kurth, J. Org. Chem. 65, 499 (2000); ref. [5f]; F. J. Freire Castro, M. M. Vila, P. R. Jenkins, M. L. Sharma, G. Tustin, J. Fawcett, D. R. Russel, Synlett 6, 798 (1999);
95. b) cf. rediscoveries: K. S.-L. Huang, E. H. Lee, M. M. Olmstead, M. J. Kurth, J. Org. Chem. 65, 499 (2000); ref. [5f]; F. J. Freire Castro, M. M. Vila, P. R. Jenkins, M. L. Sharma, G. Tustin, J. Fawcett, D. R. Russel, Synlett 6, 798 (1999);
96. b) cf. rediscoveries: K. S.-L. Huang, E. H. Lee, M. M. Olmstead, M. J. Kurth, J. Org. Chem. 65, 499 (2000); ref. [5f]; F. J. Freire Castro, M. M. Vila, P. R. Jenkins, M. L. Sharma, G. Tustin, J. Fawcett, D. R. Russel, Synlett 6, 798 (1999);
97. c) cf. K. E. Rodriques, A. Basha, J. B. Summers, D. W. Brooks, Tetrahedron Lett. 29, 3455 (1988); R. A. Volkman, in B. M. Trost, I. Fleming (eds): Comprehensive Organic Synthesis, Vol. 1, p. 386, Pergamon, Oxford (1991).
98. c) cf. K. E. Rodriques, A. Basha, J. B. Summers, D. W. Brooks, Tetrahedron Lett. 29, 3455 (1988); R. A. Volkman, in B. M. Trost, I. Fleming (eds): Comprehensive Organic Synthesis, Vol. 1, p. 386, Pergamon, Oxford (1991).
99. A. H. Blatt, N. Gross, J. Am. Chem. Soc. 77, 5424 (1955); A. Belly, C. Pétrus, F. Pétrus, Bull. Soc. Chim. Fr. 1390 (1973).
100. A. H. Blatt, N. Gross, J. Am. Chem. Soc. 77, 5424 (1955); A. Belly, C. Pétrus, F. Pétrus, Bull. Soc. Chim. Fr. 1390 (1973).
101. a) A. Cerri, C. De Micheli, R. Gandolfi, Synthesis 710 (1974);
102. b) A. P. Kozikowski, H. Ishida, J. Am. Chem. Soc. 102, 4265 (1980);
103. c) D. Cristina, M. De Amici, C. De Micheli, R. Gandolfi, Tetrahedron 37, 1349 (1981);
104. d) N. P. Peet, E. W. Huber, R. A. Farr, Tetrahedon 47, 7537 (1991).
105. S. Shatzmiller, E. Shalom, R. Lidor, E. Tartkovski, Liebigs Ann. Chem. 906 (1983).
106. J. L. Olivé, R. Jacquier, C. Pétrus, F. Pétrus, Bull. Soc. Chim. Fr. 1651 (1974); A. Belly, C. Pétrus, F. Pétrus, Bull. Soc. Chim. Fr. 1025 (1974).
107. J. L. Olivé, R. Jacquier, C. Pétrus, F. Pétrus, Bull. Soc. Chim. Fr. 1651 (1974); A. Belly, C. Pétrus, F. Pétrus, Bull. Soc. Chim. Fr. 1025 (1974).
108. S. Shatzmiller, B.-Z. Dolitzky, R. Meirowich, R. Neidlein, C. Weik, Liebigs Arm. Chem. 161 (1991).
109. a) V. Wehner, Dissertation, Universität Würzburg (1990);
110. b) B. Steuer, V. Wehner, A. Lieberknecht, V. Jäger, Org. Synth. 74, 1 (1996);
111. c) V. Jäger, V. Wehner, Angew. Chem. 101, 512 (1989); Angew. Chem. Int. Ed. 28, 469 (1989).
112. c) V. Jäger, V. Wehner, Angew. Chem. 101, 512 (1989); Angew. Chem. Int. Ed. 28, 469 (1989).
113. V. Jäger, V. Buß, W. Schwab, Tetrahedron Lett. 34, 3133 (1978); V. Jäger, V. Buß, Liebigs. Ann. Chem. 101 (1980).
114. V. Jäger, V. Buß, W. Schwab, Tetrahedron Lett. 34, 3133 (1978); V. Jäger, V. Buß, Liebigs. Ann. Chem. 101 (1980).
115. W. Frey, M. Henneböhle, V. Jäger, Z. Kristallogr. NCS, in press.
116. J. Mulzer in G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann (eds): Houben-Weyl-Müller, Methods of Organic Chemistry, Vol. E21a, Stereoselective Synthesis, p. 75, Thieme, Stuttgart (1995); A. Mengel, O. Reiser, Chem. Rev. 99, 1191 (1999).
117. J. Mulzer in G. Helmchen, R. W. Hoffmann, J. Mulzer, E. Schaumann (eds): Houben-Weyl-Müller, Methods of Organic Chemistry, Vol. E21a, Stereoselective Synthesis, p. 75, Thieme, Stuttgart (1995); A. Mengel, O. Reiser, Chem. Rev. 99, 1191 (1999).
118. R. Annzunziata, M. Cinquini, F. Cozzi, A. Gilardi, A. Restelli, J. Chem. Soc., Perkin Trans I, 2289 (1985); J. Ipaktschi, Chem. Ber. 117, 856 (1984); S. K. Armstrong, S. Warren, E. W. Collington, A. Naylor, Tetrahedron Lett. 32, 4171 (1991); H. I. Schlesinger, H. C. Brown, A. E. Finholt, J. R. Gilbreath, H. R. Hoekstra, E. K. Hyde, J. Am. Chem. Soc. 75, 215 (1953).
119. R. Annzunziata, M. Cinquini, F. Cozzi, A. Gilardi, A. Restelli, J. Chem. Soc., Perkin Trans I, 2289 (1985); J. Ipaktschi, Chem. Ber. 117, 856 (1984); S. K. Armstrong, S. Warren, E. W. Collington, A. Naylor, Tetrahedron Lett. 32, 4171 (1991); H. I. Schlesinger, H. C. Brown, A. E. Finholt, J. R. Gilbreath, H. R. Hoekstra, E. K. Hyde, J. Am. Chem. Soc. 75, 215 (1953).
120. R. Annzunziata, M. Cinquini, F. Cozzi, A. Gilardi, A. Restelli, J. Chem. Soc., Perkin Trans I, 2289 (1985); J. Ipaktschi, Chem. Ber. 117, 856 (1984); S. K. Armstrong, S. Warren, E. W. Collington, A. Naylor, Tetrahedron Lett. 32, 4171 (1991); H. I. Schlesinger, H. C. Brown, A. E. Finholt, J. R. Gilbreath, H. R. Hoekstra, E. K. Hyde, J. Am. Chem. Soc. 75, 215 (1953).
121. R. Annzunziata, M. Cinquini, F. Cozzi, A. Gilardi, A. Restelli, J. Chem. Soc., Perkin Trans I, 2289 (1985); J. Ipaktschi, Chem. Ber. 117, 856 (1984); S. K. Armstrong, S. Warren, E. W. Collington, A. Naylor, Tetrahedron Lett. 32, 4171 (1991); H. I. Schlesinger, H. C. Brown, A. E. Finholt, J. R. Gilbreath, H. R. Hoekstra, E. K. Hyde, J. Am. Chem. Soc. 75, 215 (1953).
122. M. Zhao, J. Li, Z. Song, R. Desmond, D. M. Tschaen, E. J. J. Grabowski, P. J. Reider, Tetrahedron Lett. 39, 5323 (1998).
123. M. Henneböhle, W. Frey, V. Jäger, Z. Kristallogr. NCS, in press.
124. K.-C. Liu, B. R. Shelton, R. K. Howe, J. Org. Chem. 45, 3916 (1980).
125. B. Häfele, Diplomarbeit, Universität Würzburg (1983); B. Häfele, Dissertation, Universität Würzburg (1987).
126. B. Häfele, Diplomarbeit, Universität Würzburg (1983); B. Häfele, Dissertation, Universität Würzburg (1987).
127. R. W. Hoffmann, G. Eichler, A. Endesfelder, Liebigs Ann. Chem. 2000 (1983).
128. H. Yin, R. W. Franck, S.-L. Chen, G. J. Quigley, L. Todardo, J. Org. Chem. 57, 644 (1992).
129. L. F. Fieser, M. Fieser, Reagents for Organic Synthesis, Vol. 1, p. 584, Wiley, New York (1967).
130. M. D. Armstrong, J. Am. Chem. Soc. 70, 1756 (1948).