An enantioselective synthesis of heteroaromatic N-tosyl α-amino acids

Chemical Communications

Volumn , Issue 21, 1999, Pages 2233-2234

  Johannsen, Mogens ^a  

^a TECHNICAL UNIVERSITY OF DENMARK   (Denmark)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID; AMINO ACID DERIVATIVE; COPPER COMPLEX; GLYOXYLIC ACID DERIVATIVE; INDOLE DERIVATIVE; PYRROLE DERIVATIVE; TOLUENESULFONYL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; ENANTIOMER; OPTICAL ROTATION; PARTIAL DRUG SYNTHESIS; STEREOISOMERISM;

EID: 0033533951     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a906758b     Document Type: Article

References (44)

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22. (R)-Tol-BINAP is the abbreviation for the commercial ligand (R)-(+)-2,2′-bis(di-p-tolylphosphino)-1,1′-binaphthyl.
23. 13C NMR spectra in accordance with the assigned structures. It should be mentioned that a derivative of 3a has previously been prepard via an enzymatic resolution (ref. 12). For some excellent reviews on the synthesis of α-amino acids, see: R. M. Williams, Aldrichim. Acta, 1992, 25, 11; R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon, New York, 1989; R. O. Duthaler, Tetrahedron, 1994, 50, 1539.
24. 13C NMR spectra in accordance with the assigned structures. It should be mentioned that a derivative of 3a has previously been prepard via an enzymatic resolution (ref. 12). For some excellent reviews on the synthesis of α-amino acids, see: R. M. Williams, Aldrichim. Acta, 1992, 25, 11; R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon, New York, 1989; R. O. Duthaler, Tetrahedron, 1994, 50, 1539.
25. 13C NMR spectra in accordance with the assigned structures. It should be mentioned that a derivative of 3a has previously been prepard via an enzymatic resolution (ref. 12). For some excellent reviews on the synthesis of α-amino acids, see: R. M. Williams, Aldrichim. Acta, 1992, 25, 11; R. M. Williams, Synthesis of Optically Active α-Amino Acids, Pergamon, New York, 1989; R. O. Duthaler, Tetrahedron, 1994, 50, 1539.
26. For an introduction to heterocyclic chemistry, see e.g.: J. A. Joule, K. Mills and G. F. Smith, Heterocyclic Chemistry, Stanley Thornes, Cheltenham, 1998.
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28. For some recent examples of achiral additions of imines to indoles, see e.g.: H. Heaney, G. Papageorgiou and R. F. Wilkins, Chem. Commun., 1988, 1161; H. Heaney, G. Papageorgiou and R. F. Wilkins, Tetrahedron, 1997, 53, 2941; H.-C. Zhang, K. K. Brumfield, L. Jaroskova and B. E. Maryanoff, Tetrahedron Lett., 1998, 39, 4449.
29. For some recent examples of achiral additions of imines to indoles, see e.g.: H. Heaney, G. Papageorgiou and R. F. Wilkins, Chem. Commun., 1988, 1161; H. Heaney, G. Papageorgiou and R. F. Wilkins, Tetrahedron, 1997, 53, 2941; H.-C. Zhang, K. K. Brumfield, L. Jaroskova and B. E. Maryanoff, Tetrahedron Lett., 1998, 39, 4449.
30. 3) 170.5, 143.2, 137.0, 136.2, 129.2, 127.2, 125.2, 123.4, 122.7, 120.2, 119.1, 111.3, 110.5, 62.0, 53.1, 21.5, 13.9.
31. Several methods exists for the deprotection of similar N-tosyl α-amino acids without notable racemisation: T. Shono, Y. Matsumura and T. Kanazawa, Tetrahedron Lett., 1983, 24, 1259; T. Shono, Y. Matsumura, K. Tsubata, K. Uchida, T. Kanazawa and K. Tsuda, J. Org. Chem., 1984, 49, 3711; E. Vedejs and S. Lin, J. Org. Chem., 1994, 59, 1602; See also: T. Kanazawa, T. Hamada, A. Nishida and O. Yonemitsu, J. Am. Chem. Soc., 1986, 108, 140; T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, 2nd edn., Wiley-Interscience, New York, 1991, pp. 379-381.
32. Several methods exists for the deprotection of similar N-tosyl α-amino acids without notable racemisation: T. Shono, Y. Matsumura and T. Kanazawa, Tetrahedron Lett., 1983, 24, 1259; T. Shono, Y. Matsumura, K. Tsubata, K. Uchida, T. Kanazawa and K. Tsuda, J. Org. Chem., 1984, 49, 3711; E. Vedejs and S. Lin, J. Org. Chem., 1994, 59, 1602; See also: T. Kanazawa, T. Hamada, A. Nishida and O. Yonemitsu, J. Am. Chem. Soc., 1986, 108, 140; T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, 2nd edn., Wiley-Interscience, New York, 1991, pp. 379-381.
33. Several methods exists for the deprotection of similar N-tosyl α-amino acids without notable racemisation: T. Shono, Y. Matsumura and T. Kanazawa, Tetrahedron Lett., 1983, 24, 1259; T. Shono, Y. Matsumura, K. Tsubata, K. Uchida, T. Kanazawa and K. Tsuda, J. Org. Chem., 1984, 49, 3711; E. Vedejs and S. Lin, J. Org. Chem., 1994, 59, 1602; See also: T. Kanazawa, T. Hamada, A. Nishida and O. Yonemitsu, J. Am. Chem. Soc., 1986, 108, 140; T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, 2nd edn., Wiley-Interscience, New York, 1991, pp. 379-381.
34. Several methods exists for the deprotection of similar N-tosyl α-amino acids without notable racemisation: T. Shono, Y. Matsumura and T. Kanazawa, Tetrahedron Lett., 1983, 24, 1259; T. Shono, Y. Matsumura, K. Tsubata, K. Uchida, T. Kanazawa and K. Tsuda, J. Org. Chem., 1984, 49, 3711; E. Vedejs and S. Lin, J. Org. Chem., 1994, 59, 1602; See also: T. Kanazawa, T. Hamada, A. Nishida and O. Yonemitsu, J. Am. Chem. Soc., 1986, 108, 140; T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, 2nd edn., Wiley-Interscience, New York, 1991, pp. 379-381.
35. Several methods exists for the deprotection of similar N-tosyl α-amino acids without notable racemisation: T. Shono, Y. Matsumura and T. Kanazawa, Tetrahedron Lett., 1983, 24, 1259; T. Shono, Y. Matsumura, K. Tsubata, K. Uchida, T. Kanazawa and K. Tsuda, J. Org. Chem., 1984, 49, 3711; E. Vedejs and S. Lin, J. Org. Chem., 1994, 59, 1602; See also: T. Kanazawa, T. Hamada, A. Nishida and O. Yonemitsu, J. Am. Chem. Soc., 1986, 108, 140; T. W. Greene and P. G. M. Wuts, Protective Groups in Organic Synthesis, 2nd edn., Wiley-Interscience, New York, 1991, pp. 379-381.
36. For other N-protecting groups, see: D. Ferraris, T. Dudding, B. Young, W. J. Drury III and T. Lectka, J. Org. Chem., 1999, 64, 2168.
37. Many naturally-occurring as well as biologically active indole alkaloids are substituted in the 5-position of the indole system. For some examples see e.g.: G. A. Cordell, Lloydia, 1974, 37, 219; K. B. G. Torsell, Natural Product Chemistry, 2nd edn., Apotekarsocieteten, Stockholm 1997.
38. Many naturally-occurring as well as biologically active indole alkaloids are substituted in the 5-position of the indole system. For some examples see e.g.: G. A. Cordell, Lloydia, 1974, 37, 219; K. B. G. Torsell, Natural Product Chemistry, 2nd edn., Apotekarsocieteten, Stockholm 1997.
39. Optically pure indolyl glycines have been used in the synthesis of potent antibiotics of the cephalosporin type: L. C. Blaszczak and J. R. Turner, US Patent, 4492694, 1985; for the use of racemic indolyl glycine derivtives as antiinflammatorial agents, see e.g.: T.-Y. Shen, US Patent, 3316260, 1968.
40. Optically pure indolyl glycines have been used in the synthesis of potent antibiotics of the cephalosporin type: L. C. Blaszczak and J. R. Turner, US Patent, 4492694, 1985; for the use of racemic indolyl glycine derivtives as antiinflammatorial agents, see e.g.: T.-Y. Shen, US Patent, 3316260, 1968.
41. 1H NMR have been given as > 98%, even though only one enantiomer was detected.
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