Stereospecific synthesis of chiral N-(ethynyl)allylglycines and their use in highly stereoselective intramolecular Pauson-Khand reactions

Chemical Communications

Volumn , Issue 18, 1999, Pages 1879-1880

  Witulski, Bernhard ^a   Gößmann, Matthias ^a  

^a Rheinland Pfälzische Technische Universität Kaiserslautern Landau   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLGLYCINE; AMINO ACID DERIVATIVE; PROLINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; STEREOCHEMISTRY;

EID: 0041995703     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a905898b     Document Type: Article

References (24)

1. B. Witulski and T. Stengel, Angew. Chem., Int. Ed., 1998, 37, 489.
2. P. J. Stang and V. V. Zhdankin, Chem. Rev., 1996, 96, 1123.
3. G. Himbert, Methoden Org. Chem. (Houben-Weyl), 1993, vol. E15, pp. 3267-3461; J. Ficini, Tetrahedron, 1976, 32, 1448.
4. G. Himbert, Methoden Org. Chem. (Houben-Weyl), 1993, vol. E15, pp. 3267-3461; J. Ficini, Tetrahedron, 1976, 32, 1448.
5. B. Witulski and T. Stengel, Angew. Chem., Int. Ed., 1999, 38, in the press.
6. J. Gante, Angew. Chem., Int. Ed. Engl., 1994, 33, 1699; A. E. P. Adang, P. H. H. Hermkens, J. T. M. Linders, H. C. J. Ottenheijm and C. J. van Staveren, Recl. Trav. Chim. Pays-Bas., 1994, 113, 63
7. J. Gante, Angew. Chem., Int. Ed. Engl., 1994, 33, 1699; A. E. P. Adang, P. H. H. Hermkens, J. T. M. Linders, H. C. J. Ottenheijm and C. J. van Staveren, Recl. Trav. Chim. Pays-Bas., 1994, 113, 63
8. R. Henning, U. Lerch and H. Urbach, Synthesis, 1989, 265.
9. M. T. Reetz, T. J. Strack, J. Kanand and R. Goddard, Chem. Commun., 1996, 733.
10. For the preparation of 3b and its reaction with carbon nucleophiles see: M. Ochiai, T. Ito, Y. Takaoka, Y. Masaki, M. Kunishima, S. Tani and Y. Nagao, J. Chem. Soc., Chem. Commun., 1990, 118; P. J. Stang, in Modern Acetylene Chemistry, ed. P. J. Stang and F. Diederich, VCH, Weinheim, 1995.
11. For the preparation of 3b and its reaction with carbon nucleophiles see: M. Ochiai, T. Ito, Y. Takaoka, Y. Masaki, M. Kunishima, S. Tani and Y. Nagao, J. Chem. Soc., Chem. Commun., 1990, 118; P. J. Stang, in Modern Acetylene Chemistry, ed. P. J. Stang and F. Diederich, VCH, Weinheim, 1995.
12. T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley, New York, 1991; C. Goulaouic-Dubois, A. Guggisberg and M. Hesse, J. Org. Chem., 1995, 60, 5969; T. Fukuyama, C.-K. Jow and M. Cheung, Tetrahedron Lett., 1995, 36, 6373.
13. T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley, New York, 1991; C. Goulaouic-Dubois, A. Guggisberg and M. Hesse, J. Org. Chem., 1995, 60, 5969; T. Fukuyama, C.-K. Jow and M. Cheung, Tetrahedron Lett., 1995, 36, 6373.
14. T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, Wiley, New York, 1991; C. Goulaouic-Dubois, A. Guggisberg and M. Hesse, J. Org. Chem., 1995, 60, 5969; T. Fukuyama, C.-K. Jow and M. Cheung, Tetrahedron Lett., 1995, 36, 6373.
15. M. M. Gallo, T. P. Hamilton and H. F. Schaefer III, J. Am. Chem. Soc., 1990, 112, 8714; W. Kirmse, Angew. Chem., Int. Ed. Engl., 1997, 36, 1164.
16. M. M. Gallo, T. P. Hamilton and H. F. Schaefer III, J. Am. Chem. Soc., 1990, 112, 8714; W. Kirmse, Angew. Chem., Int. Ed. Engl., 1997, 36, 1164.
17. K. S. Feldman and D. A. Mareska, J. Am. Chem. Soc., 1998, 120, 4027 and references therein.
18. 2 (24.8); all data taken from F. G. Bordwell, Acc. Chem. Res., 1988, 21, 456.
19. (S)-Allylglycine is commercially available. For its synthesis, see: Y. N. Belokon, V. I. Bakhmutov, N. I. Chernoglazova, K. A. Kochetkov, S. V. Vitt, N. S. Garbalinskaya and V. M. Belikov, J. Chem. Soc., Perkin Trans 1, 1988, 305.
20. Baseline separation of (S)-5a and (R)-5a from (rac)-Sa could be achieved by using the Chiralpak AD column.
21. For recent reviews, see A. C. Comely and S. E. Gibson, J. Chem. Soc., Perkin Trans 1, 1999, 223; O. Geis and H.-G. Schmalz, Angew. Chem., Int. Ed., 1998, 37, 911; N. E. Schore, Comprehensive Organometallic Chemistry II, ed. L. S. Hegedus, Pergamon, 1995, vol. 12, p. 703.
22. For recent reviews, see A. C. Comely and S. E. Gibson, J. Chem. Soc., Perkin Trans 1, 1999, 223; O. Geis and H.-G. Schmalz, Angew. Chem., Int. Ed., 1998, 37, 911; N. E. Schore, Comprehensive Organometallic Chemistry II, ed. L. S. Hegedus, Pergamon, 1995, vol. 12, p. 703.
23. For recent reviews, see A. C. Comely and S. E. Gibson, J. Chem. Soc., Perkin Trans 1, 1999, 223; O. Geis and H.-G. Schmalz, Angew. Chem., Int. Ed., 1998, 37, 911; N. E. Schore, Comprehensive Organometallic Chemistry II, ed. L. S. Hegedus, Pergamon, 1995, vol. 12, p. 703.
24. S. Shambayati, W. E. Crowe and S. L. Schreiber, Tetrahedron Lett., 1990, 31, 5289.