A convenient synthesis of L-α-vinylglycine from L-homoserine lactone

Synthesis

Volumn , Issue 1, 1996, Pages 39-41

  Berkowitz, David B ^a   Smith, Marianne K ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

enantiocontrolled synthesis; L homoserine lactone; L vinylglycine; phenylselenolate anion

Indexed keywords

GLYCINE DERIVATIVE; UNCLASSIFIED DRUG; VINYLGLYCINE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030019887     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1996-4177     Document Type: Article

References (48)

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13. For syntheses of (±)-α-vinylglycine, see: (a) Fitzner, J. F.; Pratt, D. V.; Hopkins, P. B. Tetrahedron Lett. 1985, 26, 1959. (b) Vyas, D. M.; Chiang, Y.; Doyle, T. W. J. Org. Chem. 1984, 49, 2037. (c) Greenlee, W. J. J. Org. Chem. 1984, 49, 2632. (d) Hudrlik, P. F.; Kulkarni, A. S. J. Am. Chem. Soc. 1981, 103, 6251. (e) Baldwin, J. E.; Haber, S. B.; Hoskins, C.; Kruse, L. I. J. Org. Chem. 1977, 42, 1239. (f) Friis, P.; Helboe, P.; Larsen, P. O. Acta Chem. Scand., Ser. B 1974, 28, 317.
14. For syntheses of (±)-α-vinylglycine, see: (a) Fitzner, J. F.; Pratt, D. V.; Hopkins, P. B. Tetrahedron Lett. 1985, 26, 1959. (b) Vyas, D. M.; Chiang, Y.; Doyle, T. W. J. Org. Chem. 1984, 49, 2037. (c) Greenlee, W. J. J. Org. Chem. 1984, 49, 2632. (d) Hudrlik, P. F.; Kulkarni, A. S. J. Am. Chem. Soc. 1981, 103, 6251. (e) Baldwin, J. E.; Haber, S. B.; Hoskins, C.; Kruse, L. I. J. Org. Chem. 1977, 42, 1239. (f) Friis, P.; Helboe, P.; Larsen, P. O. Acta Chem. Scand., Ser. B 1974, 28, 317.
15. For syntheses of (±)-α-vinylglycine, see: (a) Fitzner, J. F.; Pratt, D. V.; Hopkins, P. B. Tetrahedron Lett. 1985, 26, 1959. (b) Vyas, D. M.; Chiang, Y.; Doyle, T. W. J. Org. Chem. 1984, 49, 2037. (c) Greenlee, W. J. J. Org. Chem. 1984, 49, 2632. (d) Hudrlik, P. F.; Kulkarni, A. S. J. Am. Chem. Soc. 1981, 103, 6251. (e) Baldwin, J. E.; Haber, S. B.; Hoskins, C.; Kruse, L. I. J. Org. Chem. 1977, 42, 1239. (f) Friis, P.; Helboe, P.; Larsen, P. O. Acta Chem. Scand., Ser. B 1974, 28, 317.
16. For syntheses of (±)-α-vinylglycine, see: (a) Fitzner, J. F.; Pratt, D. V.; Hopkins, P. B. Tetrahedron Lett. 1985, 26, 1959. (b) Vyas, D. M.; Chiang, Y.; Doyle, T. W. J. Org. Chem. 1984, 49, 2037. (c) Greenlee, W. J. J. Org. Chem. 1984, 49, 2632. (d) Hudrlik, P. F.; Kulkarni, A. S. J. Am. Chem. Soc. 1981, 103, 6251. (e) Baldwin, J. E.; Haber, S. B.; Hoskins, C.; Kruse, L. I. J. Org. Chem. 1977, 42, 1239. (f) Friis, P.; Helboe, P.; Larsen, P. O. Acta Chem. Scand., Ser. B 1974, 28, 317.
17. For enantioselective syntheses of α-vinylglycine, see: (a) Pellicciari, R.; Natalini, B.; Marinozzi Synth. Commun. 1988, 18, 1715. (b) Barton, D. H. R.; Crich, D.; Herve, Y.; Potier, P.; Thiery, J. Tetrahedron 1985, 41, 4347. (c) Hanessian, S.; Sahoo, S. P. Tetrahedron Lett. 1984, 25, 1425. (d) Schöllkopf, U.; Nozulak, J.; Groth, U. Tetrahedron 1984, 40, 1409. (e) Afzali-Ardakani, A.; Rapoport, H. J. Org. Chem. 1980, 45, 4817. (f) Carrasco, M.; Jones, R. J.; Kamel, S.; Rapoport, H.; Truong, T. Org. Synth. 1991, 70, 29.
18. For enantioselective syntheses of α-vinylglycine, see: (a) Pellicciari, R.; Natalini, B.; Marinozzi Synth. Commun. 1988, 18, 1715. (b) Barton, D. H. R.; Crich, D.; Herve, Y.; Potier, P.; Thiery, J. Tetrahedron 1985, 41, 4347. (c) Hanessian, S.; Sahoo, S. P. Tetrahedron Lett. 1984, 25, 1425. (d) Schöllkopf, U.; Nozulak, J.; Groth, U. Tetrahedron 1984, 40, 1409. (e) Afzali-Ardakani, A.; Rapoport, H. J. Org. Chem. 1980, 45, 4817. (f) Carrasco, M.; Jones, R. J.; Kamel, S.; Rapoport, H.; Truong, T. Org. Synth. 1991, 70, 29.
19. For enantioselective syntheses of α-vinylglycine, see: (a) Pellicciari, R.; Natalini, B.; Marinozzi Synth. Commun. 1988, 18, 1715. (b) Barton, D. H. R.; Crich, D.; Herve, Y.; Potier, P.; Thiery, J. Tetrahedron 1985, 41, 4347. (c) Hanessian, S.; Sahoo, S. P. Tetrahedron Lett. 1984, 25, 1425. (d) Schöllkopf, U.; Nozulak, J.; Groth, U. Tetrahedron 1984, 40, 1409. (e) Afzali-Ardakani, A.; Rapoport, H. J. Org. Chem. 1980, 45, 4817. (f) Carrasco, M.; Jones, R. J.; Kamel, S.; Rapoport, H.; Truong, T. Org. Synth. 1991, 70, 29.
20. For enantioselective syntheses of α-vinylglycine, see: (a) Pellicciari, R.; Natalini, B.; Marinozzi Synth. Commun. 1988, 18, 1715. (b) Barton, D. H. R.; Crich, D.; Herve, Y.; Potier, P.; Thiery, J. Tetrahedron 1985, 41, 4347. (c) Hanessian, S.; Sahoo, S. P. Tetrahedron Lett. 1984, 25, 1425. (d) Schöllkopf, U.; Nozulak, J.; Groth, U. Tetrahedron 1984, 40, 1409. (e) Afzali-Ardakani, A.; Rapoport, H. J. Org. Chem. 1980, 45, 4817. (f) Carrasco, M.; Jones, R. J.; Kamel, S.; Rapoport, H.; Truong, T. Org. Synth. 1991, 70, 29.
21. For enantioselective syntheses of α-vinylglycine, see: (a) Pellicciari, R.; Natalini, B.; Marinozzi Synth. Commun. 1988, 18, 1715. (b) Barton, D. H. R.; Crich, D.; Herve, Y.; Potier, P.; Thiery, J. Tetrahedron 1985, 41, 4347. (c) Hanessian, S.; Sahoo, S. P. Tetrahedron Lett. 1984, 25, 1425. (d) Schöllkopf, U.; Nozulak, J.; Groth, U. Tetrahedron 1984, 40, 1409. (e) Afzali-Ardakani, A.; Rapoport, H. J. Org. Chem. 1980, 45, 4817. (f) Carrasco, M.; Jones, R. J.; Kamel, S.; Rapoport, H.; Truong, T. Org. Synth. 1991, 70, 29.
22. For enantioselective syntheses of α-vinylglycine, see: (a) Pellicciari, R.; Natalini, B.; Marinozzi Synth. Commun. 1988, 18, 1715. (b) Barton, D. H. R.; Crich, D.; Herve, Y.; Potier, P.; Thiery, J. Tetrahedron 1985, 41, 4347. (c) Hanessian, S.; Sahoo, S. P. Tetrahedron Lett. 1984, 25, 1425. (d) Schöllkopf, U.; Nozulak, J.; Groth, U. Tetrahedron 1984, 40, 1409. (e) Afzali-Ardakani, A.; Rapoport, H. J. Org. Chem. 1980, 45, 4817. (f) Carrasco, M.; Jones, R. J.; Kamel, S.; Rapoport, H.; Truong, T. Org. Synth. 1991, 70, 29.
23. Pedersen, M. L.; Berkowitz, D. B. J. Org. Chem. 1993, 58, 6966.
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25. For pioneering work on the use of phenylselenolate anion to cleave lactones, see: (a) Scarborough, R. M., Jr.; Smith, A. B. III Tetrahedron Lett. 1977, 4361. (b) Liotta, D.; Santiesteban, H. Tetrahedron Lett. 1977, 4369. (c) Scarborough, R. M., Jr.; Toder, B. H.; Smith, A. B. III J. Am. Chem. Soc. 1980, 102, 3904. (d) Liotta, D.; Ustan, S.; Santiesteben, H.; Markiewicz, W. J. Org. Chem. 1981, 46, 2605.
26. For pioneering work on the use of phenylselenolate anion to cleave lactones, see: (a) Scarborough, R. M., Jr.; Smith, A. B. III Tetrahedron Lett. 1977, 4361. (b) Liotta, D.; Santiesteban, H. Tetrahedron Lett. 1977, 4369. (c) Scarborough, R. M., Jr.; Toder, B. H.; Smith, A. B. III J. Am. Chem. Soc. 1980, 102, 3904. (d) Liotta, D.; Ustan, S.; Santiesteben, H.; Markiewicz, W. J. Org. Chem. 1981, 46, 2605.
27. For pioneering work on the use of phenylselenolate anion to cleave lactones, see: (a) Scarborough, R. M., Jr.; Smith, A. B. III Tetrahedron Lett. 1977, 4361. (b) Liotta, D.; Santiesteban, H. Tetrahedron Lett. 1977, 4369. (c) Scarborough, R. M., Jr.; Toder, B. H.; Smith, A. B. III J. Am. Chem. Soc. 1980, 102, 3904. (d) Liotta, D.; Ustan, S.; Santiesteben, H.; Markiewicz, W. J. Org. Chem. 1981, 46, 2605.
28. For pioneering work on the use of phenylselenolate anion to cleave lactones, see: (a) Scarborough, R. M., Jr.; Smith, A. B. III Tetrahedron Lett. 1977, 4361. (b) Liotta, D.; Santiesteban, H. Tetrahedron Lett. 1977, 4369. (c) Scarborough, R. M., Jr.; Toder, B. H.; Smith, A. B. III J. Am. Chem. Soc. 1980, 102, 3904. (d) Liotta, D.; Ustan, S.; Santiesteben, H.; Markiewicz, W. J. Org. Chem. 1981, 46, 2605.
29. For other phenylselenolate anion equivalents, see: (a) Hoye, T. R.; Caruso, A. J. Tetrahedron Lett. 1978, 4611. (b) Dowd, P.; Kennedy, P. Synth. Commun. 1981, 11, 935. (c) Ley, S. V.; O'Neill, I. A.; Low, C. M. R. Tetrahedron 1986, 46, 5363 (d) Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1991, 2885.
30. For other phenylselenolate anion equivalents, see: (a) Hoye, T. R.; Caruso, A. J. Tetrahedron Lett. 1978, 4611. (b) Dowd, P.; Kennedy, P. Synth. Commun. 1981, 11, 935. (c) Ley, S. V.; O'Neill, I. A.; Low, C. M. R. Tetrahedron 1986, 46, 5363 (d) Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1991, 2885.
31. For other phenylselenolate anion equivalents, see: (a) Hoye, T. R.; Caruso, A. J. Tetrahedron Lett. 1978, 4611. (b) Dowd, P.; Kennedy, P. Synth. Commun. 1981, 11, 935. (c) Ley, S. V.; O'Neill, I. A.; Low, C. M. R. Tetrahedron 1986, 46, 5363 (d) Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1991, 2885.
32. For other phenylselenolate anion equivalents, see: (a) Hoye, T. R.; Caruso, A. J. Tetrahedron Lett. 1978, 4611. (b) Dowd, P.; Kennedy, P. Synth. Commun. 1981, 11, 935. (c) Ley, S. V.; O'Neill, I. A.; Low, C. M. R. Tetrahedron 1986, 46, 5363 (d) Soucy, F.; Wernic, D.; Beaulieu, P. J. Chem. Soc., Perkin Trans. 1991, 2885.
33. For previous syntheses of higher α-vinyl amino acids (α-vinylalanine, α-vinylbutyrine and α-vinylphenylalanine) in optically enriched form, see: (a) Weber, T.; Aeschimann, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta. 1986, 69, 1365. (b) Seebach, D.; Bürger, H. M.; Schickli, C. P. Liebigs Ann. Chim. 1991, 669. (c) Colson, P.-J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918.
34. For previous syntheses of higher α-vinyl amino acids (α-vinylalanine, α-vinylbutyrine and α-vinylphenylalanine) in optically enriched form, see: (a) Weber, T.; Aeschimann, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta. 1986, 69, 1365. (b) Seebach, D.; Bürger, H. M.; Schickli, C. P. Liebigs Ann. Chim. 1991, 669. (c) Colson, P.-J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918.
35. For previous syntheses of higher α-vinyl amino acids (α-vinylalanine, α-vinylbutyrine and α-vinylphenylalanine) in optically enriched form, see: (a) Weber, T.; Aeschimann, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta. 1986, 69, 1365. (b) Seebach, D.; Bürger, H. M.; Schickli, C. P. Liebigs Ann. Chim. 1991, 669. (c) Colson, P.-J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918.
36. For a related application of chiral dianions to synthesize enantiomerically enriched α-methyl amino acids, see: Berkowitz, D. B.; Smith, M. K. J. Org. Chem. 1995, 60, 1233.
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38. Berkowitz, D. B. Synth. Commun. 1990, 20, 1819.
39. 1H NMR spectrum thereby obtained was compared to that of the Mosher ester or amide derived from (±)-α-methoxy-α-(trifluoromethyl)phenylacetyl chloride.
40. Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543.
41. 3, 500 MHz) of this Mosher amide was compared with that of the diastereomeric Mosher amides obtained by the same sequence, starting from (±)-vinylglycine. The vinylic methine protons, the methyl ether singlets and the methyl ester singlets are resolved in the spectrum of the two diastereomers
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46. One may also begin with L-homoserine lactone, which is commercially available as its hydrochloride salt. However, L-homoserine is a more economical starting material.
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