Synthesis of quaternary amino acids bearing a (2′Z)-fluorovinyl α-branch: Potential PLP enzyme inactivators

Organic Letters

Volumn 6, Issue 11, 2004, Pages 1821-1824

  Berkowitz, David B ^a   De La Salud Bea, Roberto ^a   Jahng, Wan Jin ^a  

^a UNIVERSITY OF NEBRASKA LINCOLN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; DIETHYL ALPHA FLUORO ALPHA (PHENYLSULFONYL)METHYLPHOSPHONATE; ENZYME INHIBITOR; FORMIC ACID; METHYL GROUP; PHOSPHONIC ACID DERIVATIVE; PYRIDOXAL 5 PHOSPHATE; REAGENT; SULFONE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL PROCEDURES; CHEMICAL REACTION; DRUG SYNTHESIS; STEREOCHEMISTRY;

AMINO ACIDS; AROMATIC-L-AMINO-ACID DECARBOXYLASES; FLUORINE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; STEREOISOMERISM; SULFONES; TIN COMPOUNDS; VINYL COMPOUNDS;

EID: 2942568530     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049422u     Document Type: Article

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21. For other examples of HWE-type condensations with 6, see: (a) McCarthy, J. R.; Matthews, D. P.; Paolini, J. P. Org. Synth. 1995, 72, 216-24. (b) Gross, R. S.; Mehdi, S.; McCarthy, J. R. Tetrahedron Lett. 1993, 34, 7197-7200 . (c) McCarthy, J. R.; Matthews, D. P.; Stemerick, D. M.; Huber, E. W.; Bey, P.; Lippert, B. J.; Snyder, R. D.; Sunkara, P. S. J. Am. Chem. Soc. 1991, 113, 7439-7440
22. (a) Pedersen, M. L.; Berkowitz, D. B. J. Org. Chem. 1993, 58, 6966-6975.
23. (b) Pedersen, M. L.; Berkowitz, D. B. Tetrahedron Lett. 1992, 33, 7315-7318.
24. See also: (c) Columbo, L.; Di Giacomo, M.; Vinci, V.; Columbo, M.; Manzoni, L.; Scolastico, C. Tetrahedron 2003, 59, 4501-4513.
25. For enantioselective syntheses of quaternary, α-vinyl AA's, see: (a) Ma, D.; Zhu, W. J. Org. Chem. 2001, 66, 348-350. (b) Berkowitz, D. B.; McFadden, J. M.; Chisowa, E.; Semerad, C. L. J. Am. Chem. Soc. 2000, 122, 11031-11032. (c) Berkowitz, D. B.; McFadden, J. M.; Sloss, M. K. J. Org. Chem. 2000, 65, 2907-2918. (d) Avenoza, A.; Cativiela, C.; Corzana, F.; Peregrina, J. M.; Zurbano, M. M. J. Org. Chem. 1999, 64, 8220-8225. (e) Berkowitz, D. B.; Pumphrey, J. A.; Shen, Q. Tetrahedron Lett. 1994, 35, 8743-8747 (f) Colson, P.-J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918-5924. (g) Seebach, D.; Bürger, H. M.; Schickli, C. P. Liebigs Ann. Chim. 1991, 669-684. (h) Weber, T.; Aeschimann, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta 1986, 69, 1365-1377. (i) Groth, U.; Schöllkopf, U.; Chiang, Y.-C. Synthesis 1982, 864-866.
26. For enantioselective syntheses of quaternary, α-vinyl AA's, see: (a) Ma, D.; Zhu, W. J. Org. Chem. 2001, 66, 348-350. (b) Berkowitz, D. B.; McFadden, J. M.; Chisowa, E.; Semerad, C. L. J. Am. Chem. Soc. 2000, 122, 11031-11032. (c) Berkowitz, D. B.; McFadden, J. M.; Sloss, M. K. J. Org. Chem. 2000, 65, 2907-2918. (d) Avenoza, A.; Cativiela, C.; Corzana, F.; Peregrina, J. M.; Zurbano, M. M. J. Org. Chem. 1999, 64, 8220-8225. (e) Berkowitz, D. B.; Pumphrey, J. A.; Shen, Q. Tetrahedron Lett. 1994, 35, 8743-8747 (f) Colson, P.-J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918-5924. (g) Seebach, D.; Bürger, H. M.; Schickli, C. P. Liebigs Ann. Chim. 1991, 669-684. (h) Weber, T.; Aeschimann, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta 1986, 69, 1365-1377. (i) Groth, U.; Schöllkopf, U.; Chiang, Y.-C. Synthesis 1982, 864-866.
27. For enantioselective syntheses of quaternary, α-vinyl AA's, see: (a) Ma, D.; Zhu, W. J. Org. Chem. 2001, 66, 348-350. (b) Berkowitz, D. B.; McFadden, J. M.; Chisowa, E.; Semerad, C. L. J. Am. Chem. Soc. 2000, 122, 11031-11032. (c) Berkowitz, D. B.; McFadden, J. M.; Sloss, M. K. J. Org. Chem. 2000, 65, 2907-2918. (d) Avenoza, A.; Cativiela, C.; Corzana, F.; Peregrina, J. M.; Zurbano, M. M. J. Org. Chem. 1999, 64, 8220-8225. (e) Berkowitz, D. B.; Pumphrey, J. A.; Shen, Q. Tetrahedron Lett. 1994, 35, 8743-8747 (f) Colson, P.-J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918-5924. (g) Seebach, D.; Bürger, H. M.; Schickli, C. P. Liebigs Ann. Chim. 1991, 669-684. (h) Weber, T.; Aeschimann, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta 1986, 69, 1365-1377. (i) Groth, U.; Schöllkopf, U.; Chiang, Y.-C. Synthesis 1982, 864-866.
28. For enantioselective syntheses of quaternary, α-vinyl AA's, see: (a) Ma, D.; Zhu, W. J. Org. Chem. 2001, 66, 348-350. (b) Berkowitz, D. B.; McFadden, J. M.; Chisowa, E.; Semerad, C. L. J. Am. Chem. Soc. 2000, 122, 11031-11032. (c) Berkowitz, D. B.; McFadden, J. M.; Sloss, M. K. J. Org. Chem. 2000, 65, 2907-2918. (d) Avenoza, A.; Cativiela, C.; Corzana, F.; Peregrina, J. M.; Zurbano, M. M. J. Org. Chem. 1999, 64, 8220-8225. (e) Berkowitz, D. B.; Pumphrey, J. A.; Shen, Q. Tetrahedron Lett. 1994, 35, 8743-8747 (f) Colson, P.-J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918-5924. (g) Seebach, D.; Bürger, H. M.; Schickli, C. P. Liebigs Ann. Chim. 1991, 669-684. (h) Weber, T.; Aeschimann, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta 1986, 69, 1365-1377. (i) Groth, U.; Schöllkopf, U.; Chiang, Y.-C. Synthesis 1982, 864-866.
29. For enantioselective syntheses of quaternary, α-vinyl AA's, see: (a) Ma, D.; Zhu, W. J. Org. Chem. 2001, 66, 348-350. (b) Berkowitz, D. B.; McFadden, J. M.; Chisowa, E.; Semerad, C. L. J. Am. Chem. Soc. 2000, 122, 11031-11032. (c) Berkowitz, D. B.; McFadden, J. M.; Sloss, M. K. J. Org. Chem. 2000, 65, 2907-2918. (d) Avenoza, A.; Cativiela, C.; Corzana, F.; Peregrina, J. M.; Zurbano, M. M. J. Org. Chem. 1999, 64, 8220-8225. (e) Berkowitz, D. B.; Pumphrey, J. A.; Shen, Q. Tetrahedron Lett. 1994, 35, 8743-8747 (f) Colson, P.-J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918-5924. (g) Seebach, D.; Bürger, H. M.; Schickli, C. P. Liebigs Ann. Chim. 1991, 669-684. (h) Weber, T.; Aeschimann, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta 1986, 69, 1365-1377. (i) Groth, U.; Schöllkopf, U.; Chiang, Y.-C. Synthesis 1982, 864-866.
30. For enantioselective syntheses of quaternary, α-vinyl AA's, see: (a) Ma, D.; Zhu, W. J. Org. Chem. 2001, 66, 348-350. (b) Berkowitz, D. B.; McFadden, J. M.; Chisowa, E.; Semerad, C. L. J. Am. Chem. Soc. 2000, 122, 11031-11032. (c) Berkowitz, D. B.; McFadden, J. M.; Sloss, M. K. J. Org. Chem. 2000, 65, 2907-2918. (d) Avenoza, A.; Cativiela, C.; Corzana, F.; Peregrina, J. M.; Zurbano, M. M. J. Org. Chem. 1999, 64, 8220-8225. (e) Berkowitz, D. B.; Pumphrey, J. A.; Shen, Q. Tetrahedron Lett. 1994, 35, 8743-8747 (f) Colson, P.-J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918-5924. (g) Seebach, D.; Bürger, H. M.; Schickli, C. P. Liebigs Ann. Chim. 1991, 669-684. (h) Weber, T.; Aeschimann, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta 1986, 69, 1365-1377. (i) Groth, U.; Schöllkopf, U.; Chiang, Y.-C. Synthesis 1982, 864-866.
31. For enantioselective syntheses of quaternary, α-vinyl AA's, see: (a) Ma, D.; Zhu, W. J. Org. Chem. 2001, 66, 348-350. (b) Berkowitz, D. B.; McFadden, J. M.; Chisowa, E.; Semerad, C. L. J. Am. Chem. Soc. 2000, 122, 11031-11032. (c) Berkowitz, D. B.; McFadden, J. M.; Sloss, M. K. J. Org. Chem. 2000, 65, 2907-2918. (d) Avenoza, A.; Cativiela, C.; Corzana, F.; Peregrina, J. M.; Zurbano, M. M. J. Org. Chem. 1999, 64, 8220-8225. (e) Berkowitz, D. B.; Pumphrey, J. A.; Shen, Q. Tetrahedron Lett. 1994, 35, 8743-8747 (f) Colson, P.-J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918-5924. (g) Seebach, D.; Bürger, H. M.; Schickli, C. P. Liebigs Ann. Chim. 1991, 669-684. (h) Weber, T.; Aeschimann, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta 1986, 69, 1365-1377. (i) Groth, U.; Schöllkopf, U.; Chiang, Y.-C. Synthesis 1982, 864-866.
32. For enantioselective syntheses of quaternary, α-vinyl AA's, see: (a) Ma, D.; Zhu, W. J. Org. Chem. 2001, 66, 348-350. (b) Berkowitz, D. B.; McFadden, J. M.; Chisowa, E.; Semerad, C. L. J. Am. Chem. Soc. 2000, 122, 11031-11032. (c) Berkowitz, D. B.; McFadden, J. M.; Sloss, M. K. J. Org. Chem. 2000, 65, 2907-2918. (d) Avenoza, A.; Cativiela, C.; Corzana, F.; Peregrina, J. M.; Zurbano, M. M. J. Org. Chem. 1999, 64, 8220-8225. (e) Berkowitz, D. B.; Pumphrey, J. A.; Shen, Q. Tetrahedron Lett. 1994, 35, 8743-8747 (f) Colson, P.-J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918-5924. (g) Seebach, D.; Bürger, H. M.; Schickli, C. P. Liebigs Ann. Chim. 1991, 669-684. (h) Weber, T.; Aeschimann, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta 1986, 69, 1365-1377. (i) Groth, U.; Schöllkopf, U.; Chiang, Y.-C. Synthesis 1982, 864-866.
33. For enantioselective syntheses of quaternary, α-vinyl AA's, see: (a) Ma, D.; Zhu, W. J. Org. Chem. 2001, 66, 348-350. (b) Berkowitz, D. B.; McFadden, J. M.; Chisowa, E.; Semerad, C. L. J. Am. Chem. Soc. 2000, 122, 11031-11032. (c) Berkowitz, D. B.; McFadden, J. M.; Sloss, M. K. J. Org. Chem. 2000, 65, 2907-2918. (d) Avenoza, A.; Cativiela, C.; Corzana, F.; Peregrina, J. M.; Zurbano, M. M. J. Org. Chem. 1999, 64, 8220-8225. (e) Berkowitz, D. B.; Pumphrey, J. A.; Shen, Q. Tetrahedron Lett. 1994, 35, 8743-8747 (f) Colson, P.-J.; Hegedus, L. S. J. Org. Chem. 1993, 58, 5918-5924. (g) Seebach, D.; Bürger, H. M.; Schickli, C. P. Liebigs Ann. Chim. 1991, 669-684. (h) Weber, T.; Aeschimann, R.; Maetzke, T.; Seebach, D. Helv. Chim. Acta 1986, 69, 1365-1377. (i) Groth, U.; Schöllkopf, U.; Chiang, Y.-C. Synthesis 1982, 864-866.
34. In support of this, McCarthy does observe a stereospecific conversion of β,β-disubstituted fluorovinyl phenyl sulfones to the corresponding stannanes (ref 11). However, in the absence of data for the stannylation of the (Z)-isomers of 7, one cannot rigorously rule out an equilibration mechanism here. In this context, it is well to note that vinyl stannanes are known to isomerize upon heating in the presence of tin hydrides: Leusink, A. J.; Budding, H. A. J. Organomet. Chem. 1968, 11, 541-547.
35. For a related cross-coupling approach to α-branch extension for nonfluorinated quaternary AA's, see: Berkowitz, D. B.; Chisowa, E.; McFadden, J. M. Tetrahedron 2001, 57, 6329-6343.
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