A new synthesis of α-amino acid thioesters by pummerer reaction of 3- substituted-4-sulfinyl-β-sultams

Journal of Organic Chemistry

Volumn 63, Issue 23, 1998, Pages 8355-8360

  Iwama, Tetsuo ^a   Kataoka, Tadashi ^a   Muraoka, Osamu ^b   Tanabe, Genzoh ^b  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

^b KINKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA AMINO ACID THIOESTER; BETA SULTAM DERIVATIVE; IMINE; THIOESTER; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DIASTEREOISOMER; HYDROLYSIS; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; SOLID PHASE EXTRACTION; STEREOCHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 0032515120     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981230n     Document Type: Article

References (38)

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17. For some recent papers, see (a) Sasaki, S.; Shinoya, M.; Koga, K. J. Am. Chem. Soc. 1985, 107, 3371-3372. (b) Sasaki, S.; Koga, K, Chem. Pharm. Bull. 1989, 37, 912-919. Schnölzer, M.; Kent, S. B. H. Science 1992, 256, 221-226. Hojo, H.; Know, Y.; Kakuta, Y.; Tsuda, S.; Tanaka, I.; Hikichi, K.; Aimoto, S. Bull. Chem. Soc. Jpn. 1993, 66, 2700-2706. (e) Richter, L. S.; Tom, J. Y. K.; Burnier, J. P. Tetrahedron Lett. 1994, 35, 5547-5550. (f) Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. H. Science 1994, 266, 776-779. (g) Tam, J. P.; Lu, Y. A.; Liu, C. f.; Shao, J. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 12485-12489. (h) Hojo, H.; Yoshimura, S.; Go, M.; Aimoto, S. Bull. Chem. Soc. Jpn. 1995, 68, 330-336. Aimoto, S.; Hojo, H.; Yoshimura, S.; Shimizu, N.; Asano, T.; Ikebe, M.; Kokui, T.; Crivici, A.; Ikura, M. Pept. Chem. 1995, Volume Date 1994, 32nd, 197-200 [Chemical Abstract on CD-ROM, 125: 11415]. (j) Kawakami, T.; Kogure, S.; Aimoto, S. Bull. Chem. Soc. Jpn. 1996, 69, 3331-3338. (k) Shao, Y.; Lu, W.; Kent, S. B. H. Tetrahedron Lett. 1998, 39, 3911-3914.
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20. For some recent papers, see (a) Sasaki, S.; Shinoya, M.; Koga, K. J. Am. Chem. Soc. 1985, 107, 3371-3372. (b) Sasaki, S.; Koga, K, Chem. Pharm. Bull. 1989, 37, 912-919. Schnölzer, M.; Kent, S. B. H. Science 1992, 256, 221-226. Hojo, H.; Know, Y.; Kakuta, Y.; Tsuda, S.; Tanaka, I.; Hikichi, K.; Aimoto, S. Bull. Chem. Soc. Jpn. 1993, 66, 2700-2706. (e) Richter, L. S.; Tom, J. Y. K.; Burnier, J. P. Tetrahedron Lett. 1994, 35, 5547-5550. (f) Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. H. Science 1994, 266, 776-779. (g) Tam, J. P.; Lu, Y. A.; Liu, C. f.; Shao, J. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 12485-12489. (h) Hojo, H.; Yoshimura, S.; Go, M.; Aimoto, S. Bull. Chem. Soc. Jpn. 1995, 68, 330-336. Aimoto, S.; Hojo, H.; Yoshimura, S.; Shimizu, N.; Asano, T.; Ikebe, M.; Kokui, T.; Crivici, A.; Ikura, M. Pept. Chem. 1995, Volume Date 1994, 32nd, 197-200 [Chemical Abstract on CD-ROM, 125: 11415]. (j) Kawakami, T.; Kogure, S.; Aimoto, S. Bull. Chem. Soc. Jpn. 1996, 69, 3331-3338. (k) Shao, Y.; Lu, W.; Kent, S. B. H. Tetrahedron Lett. 1998, 39, 3911-3914.
21. For some recent papers, see (a) Sasaki, S.; Shinoya, M.; Koga, K. J. Am. Chem. Soc. 1985, 107, 3371-3372. (b) Sasaki, S.; Koga, K, Chem. Pharm. Bull. 1989, 37, 912-919. Schnölzer, M.; Kent, S. B. H. Science 1992, 256, 221-226. Hojo, H.; Know, Y.; Kakuta, Y.; Tsuda, S.; Tanaka, I.; Hikichi, K.; Aimoto, S. Bull. Chem. Soc. Jpn. 1993, 66, 2700-2706. (e) Richter, L. S.; Tom, J. Y. K.; Burnier, J. P. Tetrahedron Lett. 1994, 35, 5547-5550. (f) Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. H. Science 1994, 266, 776-779. (g) Tam, J. P.; Lu, Y. A.; Liu, C. f.; Shao, J. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 12485-12489. (h) Hojo, H.; Yoshimura, S.; Go, M.; Aimoto, S. Bull. Chem. Soc. Jpn. 1995, 68, 330-336. Aimoto, S.; Hojo, H.; Yoshimura, S.; Shimizu, N.; Asano, T.; Ikebe, M.; Kokui, T.; Crivici, A.; Ikura, M. Pept. Chem. 1995, Volume Date 1994, 32nd, 197-200 [Chemical Abstract on CD-ROM, 125: 11415]. (j) Kawakami, T.; Kogure, S.; Aimoto, S. Bull. Chem. Soc. Jpn. 1996, 69, 3331-3338. (k) Shao, Y.; Lu, W.; Kent, S. B. H. Tetrahedron Lett. 1998, 39, 3911-3914.
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24. For some recent papers, see (a) Sasaki, S.; Shinoya, M.; Koga, K. J. Am. Chem. Soc. 1985, 107, 3371-3372. (b) Sasaki, S.; Koga, K, Chem. Pharm. Bull. 1989, 37, 912-919. Schnölzer, M.; Kent, S. B. H. Science 1992, 256, 221-226. Hojo, H.; Know, Y.; Kakuta, Y.; Tsuda, S.; Tanaka, I.; Hikichi, K.; Aimoto, S. Bull. Chem. Soc. Jpn. 1993, 66, 2700-2706. (e) Richter, L. S.; Tom, J. Y. K.; Burnier, J. P. Tetrahedron Lett. 1994, 35, 5547-5550. (f) Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. H. Science 1994, 266, 776-779. (g) Tam, J. P.; Lu, Y. A.; Liu, C. f.; Shao, J. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 12485-12489. (h) Hojo, H.; Yoshimura, S.; Go, M.; Aimoto, S. Bull. Chem. Soc. Jpn. 1995, 68, 330-336. Aimoto, S.; Hojo, H.; Yoshimura, S.; Shimizu, N.; Asano, T.; Ikebe, M.; Kokui, T.; Crivici, A.; Ikura, M. Pept. Chem. 1995, Volume Date 1994, 32nd, 197-200 [Chemical Abstract on CD-ROM, 125: 11415]. (j) Kawakami, T.; Kogure, S.; Aimoto, S. Bull. Chem. Soc. Jpn. 1996, 69, 3331-3338. (k) Shao, Y.; Lu, W.; Kent, S. B. H. Tetrahedron Lett. 1998, 39, 3911-3914.
25. For some recent papers, see (a) Sasaki, S.; Shinoya, M.; Koga, K. J. Am. Chem. Soc. 1985, 107, 3371-3372. (b) Sasaki, S.; Koga, K, Chem. Pharm. Bull. 1989, 37, 912-919. Schnölzer, M.; Kent, S. B. H. Science 1992, 256, 221-226. Hojo, H.; Know, Y.; Kakuta, Y.; Tsuda, S.; Tanaka, I.; Hikichi, K.; Aimoto, S. Bull. Chem. Soc. Jpn. 1993, 66, 2700-2706. (e) Richter, L. S.; Tom, J. Y. K.; Burnier, J. P. Tetrahedron Lett. 1994, 35, 5547-5550. (f) Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. H. Science 1994, 266, 776-779. (g) Tam, J. P.; Lu, Y. A.; Liu, C. f.; Shao, J. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 12485-12489. (h) Hojo, H.; Yoshimura, S.; Go, M.; Aimoto, S. Bull. Chem. Soc. Jpn. 1995, 68, 330-336. Aimoto, S.; Hojo, H.; Yoshimura, S.; Shimizu, N.; Asano, T.; Ikebe, M.; Kokui, T.; Crivici, A.; Ikura, M. Pept. Chem. 1995, Volume Date 1994, 32nd, 197-200 [Chemical Abstract on CD-ROM, 125: 11415]. (j) Kawakami, T.; Kogure, S.; Aimoto, S. Bull. Chem. Soc. Jpn. 1996, 69, 3331-3338. (k) Shao, Y.; Lu, W.; Kent, S. B. H. Tetrahedron Lett. 1998, 39, 3911-3914.
26. For some recent papers see (a) Fukuyama, T.; Lin, S. C.; Li, L. J. Am. Chem. Soc. 1990, 112, 7050-7051. (b) Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J. Chem. Soc., Perkin Trans. 1 1992, 2615-2624. Ho, P. T.; Ngu, K.-y. J. Org. Chem. 1993, 58, 2313-2316. (d) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. J. Org. Chem. 1995, 60, 6431-6440.
27. For some recent papers see (a) Fukuyama, T.; Lin, S. C.; Li, L. J. Am. Chem. Soc. 1990, 112, 7050-7051. (b) Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J. Chem. Soc., Perkin Trans. 1 1992, 2615-2624. Ho, P. T.; Ngu, K.-y. J. Org. Chem. 1993, 58, 2313-2316. (d) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. J. Org. Chem. 1995, 60, 6431-6440.
28. For some recent papers see (a) Fukuyama, T.; Lin, S. C.; Li, L. J. Am. Chem. Soc. 1990, 112, 7050-7051. (b) Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J. Chem. Soc., Perkin Trans. 1 1992, 2615-2624. Ho, P. T.; Ngu, K.-y. J. Org. Chem. 1993, 58, 2313-2316. (d) Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. J. Org. Chem. 1995, 60, 6431-6440.
29. For some recent papers see (a) Fukuyama, T.; Lin, S. C.; Li, L. J. Am. Chem. Soc. 1990, 112, 7050-7051. (b) Moss, W. O.; Jones, A. C.; Wisedale, R.; Mahon, M. F.; Molloy, K. C.; Bradbury, R. H.; Hales, N. J.; Gallagher, T. J. Chem. Soc., Perkin Trans. 1 1992, 2615-2624. Ho, P. T.; Ngu, K.-y. J. Org. Chem. 1993, 58, 2313-2316. Jackson, R. F. W.; Palmer, N. J.; Wythes, M. J.; Clegg, W.; Elsegood, M. R. J. J. Org. Chem. 1995, 60, 6431-6440.
30. Williams, R. M. In Synthesis of Optically Active α-Amino Acids; Pergamon: New York, 1989.
31. Tsuge, O.; Iwanami, S. Bull. Chem. Soc. Jpn. 1970, 43, 3543-3549.
32. Gordeev, M. F.; Gordon, E. M.; Patel, D. V. J. Org. Chem. 1997, 62, 8177-8181.
33. 1H NMR spectrum of a mixture of 3b and 1b. The cis-isomers 3 can be converted to the trans-isomers 2 by treatment with LDA in THF at -78 °C.
34. Müller, M.; Otto, H.-H. Arch. Pharm. (Weinheim, Ger.) 1991, 324, 15-17.
35. 1H NMR spectrum of the mixture showed four couples of doublets at δ 4.44 and 5.37 with J = 8.3 Hz, δ 4.92 and 5.23 with J = 7.8 Hz (6A,B), δ 4.70 and 4.91 with J = 4.9 Hz, and δ 4.24 and 4.85 with J = 5.4 Hz (4dA,dB) owing to 3-and 4-protons. No trans-isomers 4A,B isomerized to cis-isomers with silica gel column chromatography.
36. 1H NMR spectrum of the recovered sulfoxide showed isomerization of the sulfoxide moiety. Two sets of doublet assigned to 3-and 4-protons of 4aA and 4aB were observed in the spectrum.
37. Hoffmann, R. W. Chem. Rev. 1989, 89, 1841-1860.
38. In prolonged reaction or prolonged workup, the diastereomeric excess decreased to ca. 75% in the worst case. Rapid workup and purification are necessary to minimize epimerization.