Stereoselective Synthesis of Freidinger Lactams Using Oxaziridines Derived from Amino Acids

Journal of Organic Chemistry

Volumn 62, Issue 3, 1997, Pages 654-663

  Wolfe, Michael S ^a,b   Dutta, Dinah ^a   Aubé, Jeffrey ^a  

^a UNIVERSITY OF KANSAS   (United States)

^b UNIVERSITY OF TENNESSEE HEALTH SCIENCE CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LACTAM DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY CRYSTALLOGRAPHY;

EID: 0031037156     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961670j     Document Type: Article

References (42)

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2. Plattner, J. J.; Norbeck, D. J., In Drug Discovery Technologies; Clark, C. R., Moos, W. H., Eds.; John Wiley & Sons: New York, 1990; pp 92-126.
3. Olson, G. L.; Bolin, D. R.; Bonner, M. P.; Bös, M.; Cook, C. M.; Fry, D. C.; Graves, B. J.; Hatada, M.; Hill, D. E.; Kahn, M.; Madison, V. S.; Rusiecki, V. K.; Sarabu, R.; Sepinwall, J.; Vincent, G. P.; Voss, M. E. J. Med. Chem. 1993, 36, 3039-3049.
4. (a) Freidinger, R. M.; Veber, D. F.; Perlow, D. S.; Brooks, J. R.; Saperstein, R. Science 1980, 210, 656-658.
5. (b) Freidinger, R. M.; Perlow, D. S.; Veber, D. F. J. Org. Chem. 1982, 47, 104-109.
6. (c) Freidinger, R. M., In Peptides: Synthesis, Structure, Function; Rich, D. H., Gross, E., Eds.; Pierce Chemical Co.: Rockford, IL, 1981; pp 673-683.
7. (d) Veber, D. F.; Freidinger, R. M. Trends Neurosci. 1985, 392-396.
8. (a) Samanen, J.; Hempel, J. C.; Narindray, D.; Regoli, D. In Chemistry and Biology: Proceedings of the Tenth American Peptide Symposium; Marshall, G. R., Ed.; ESCOM: Leiden, 1988; pp 123-125.
9. (b) Samanen, J.; Cash, T.; Narindray, D.; Brandeis, E.; Adams, W., Jr.; Weideman, H.; Yellin, T. J. Med. Chem. 1991, 34, 3036-3043.
10. (c) Ede, N. J.; Rae, I. D.; Hearn, M. T. W. Tetrahedron Lett. 1990, 31, 6071-6074.
11. In addition to monocyclic lactams of various ring sizes, the following list contains some lead references to derivatives of Freidinger lactams bearing heteroatom substituents. Selected references to related compounds containing additional cyclizations (fused or spiro) are included as well. (a) Thorsett, E. D.; Harris, E. E.; Aster, S.; Peterson, E. R; Taub, D.; Patchett, A. A. Biochem. Biophys, Res. Commun. 1983, 111, 166-171. (b) Thorsett, E. D.; Harris, E. E.; Aster, S. D.; Peterson, E. R.; Tristram, E. W.; Snyder, J. P.; Springer, J. P.; Patchett, A. A.; Ulm, E. H., In Peptides: Structure and Function; Hruby, V. J., Rich, D. H., Ed.; Pierce Chemical Co.: Rockford, IL, 1983; pp 555-558. (c) Watthey, J. W. H.; Stanton, J. L.; Desai, M.; Babiarz, J. E.; Finn, B. M. J. Med. Chem. 1985, 28, 1511-1516. (d) Thorsett, E. D.; Harris, E. E.; Aster, S. D.; Peterson, E. R.; Snyder, J. P.; Springer, J. P.; Hirshfield, J.; Tristram, E. W.; Patchett, A. A.; Ulm, E. H.; Vassil, T. C. J. Med. Chem. 1986, 29, 251-260. (e) Yanagisawa, H.; Ishihara, S.; Ando, A.; Kanazaki, T.; Miyamoto, S.; Koike, H.; Iijima, Y.; Oizumi, K.; Matsushita, Y.; Hata, T. J. Med. Chem. 1987, 30, 1984-1991. (f) Flynn, G. A.; Giroux, E. L.; Dage, R. C. J. Am. Chem. Soc. 1987, 109, 7914-7915. (g) Yanagisawa, H.; Ishihara, S.; Ando, A.; Kanazaki, T.; Miyamoto, S.; Koike, H.; Iijima, Y.; Oizumi, K.; Matsushita, Y.; Hata, T. J. Med. Chem. 1988, 31, 422-428. (h) Burkholder, T. P.; Huber, E. W.; Flynn, G. A. Bioorg. Med. Chem. Lett. 1992, 3, 231-234. (i) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Barown, B.; Ryono, D. E.; Bird, J. E.; Asaad, M. M.; Schaeffer, T. R.; Trippodo, N. C. J. Med. Chem. 1996, 39, 494-502.
12. In addition to monocyclic lactams of various ring sizes, the following list contains some lead references to derivatives of Freidinger lactams bearing heteroatom substituents. Selected references to related compounds containing additional cyclizations (fused or spiro) are included as well. (a) Thorsett, E. D.; Harris, E. E.; Aster, S.; Peterson, E. R; Taub, D.; Patchett, A. A. Biochem. Biophys, Res. Commun. 1983, 111, 166-171. (b) Thorsett, E. D.; Harris, E. E.; Aster, S. D.; Peterson, E. R.; Tristram, E. W.; Snyder, J. P.; Springer, J. P.; Patchett, A. A.; Ulm, E. H., In Peptides: Structure and Function; Hruby, V. J., Rich, D. H., Ed.; Pierce Chemical Co.: Rockford, IL, 1983; pp 555-558. (c) Watthey, J. W. H.; Stanton, J. L.; Desai, M.; Babiarz, J. E.; Finn, B. M. J. Med. Chem. 1985, 28, 1511-1516. (d) Thorsett, E. D.; Harris, E. E.; Aster, S. D.; Peterson, E. R.; Snyder, J. P.; Springer, J. P.; Hirshfield, J.; Tristram, E. W.; Patchett, A. A.; Ulm, E. H.; Vassil, T. C. J. Med. Chem. 1986, 29, 251-260. (e) Yanagisawa, H.; Ishihara, S.; Ando, A.; Kanazaki, T.; Miyamoto, S.; Koike, H.; Iijima, Y.; Oizumi, K.; Matsushita, Y.; Hata, T. J. Med. Chem. 1987, 30, 1984-1991. (f) Flynn, G. A.; Giroux, E. L.; Dage, R. C. J. Am. Chem. Soc. 1987, 109, 7914-7915. (g) Yanagisawa, H.; Ishihara, S.; Ando, A.; Kanazaki, T.; Miyamoto, S.; Koike, H.; Iijima, Y.; Oizumi, K.; Matsushita, Y.; Hata, T. J. Med. Chem. 1988, 31, 422-428. (h) Burkholder, T. P.; Huber, E. W.; Flynn, G. A. Bioorg. Med. Chem. Lett. 1992, 3, 231-234. (i) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Barown, B.; Ryono, D. E.; Bird, J. E.; Asaad, M. M.; Schaeffer, T. R.; Trippodo, N. C. J. Med. Chem. 1996, 39, 494-502.
13. In addition to monocyclic lactams of various ring sizes, the following list contains some lead references to derivatives of Freidinger lactams bearing heteroatom substituents. Selected references to related compounds containing additional cyclizations (fused or spiro) are included as well. (a) Thorsett, E. D.; Harris, E. E.; Aster, S.; Peterson, E. R; Taub, D.; Patchett, A. A. Biochem. Biophys, Res. Commun. 1983, 111, 166-171. (b) Thorsett, E. D.; Harris, E. E.; Aster, S. D.; Peterson, E. R.; Tristram, E. W.; Snyder, J. P.; Springer, J. P.; Patchett, A. A.; Ulm, E. H., In Peptides: Structure and Function; Hruby, V. J., Rich, D. H., Ed.; Pierce Chemical Co.: Rockford, IL, 1983; pp 555-558. (c) Watthey, J. W. H.; Stanton, J. L.; Desai, M.; Babiarz, J. E.; Finn, B. M. J. Med. Chem. 1985, 28, 1511-1516. (d) Thorsett, E. D.; Harris, E. E.; Aster, S. D.; Peterson, E. R.; Snyder, J. P.; Springer, J. P.; Hirshfield, J.; Tristram, E. W.; Patchett, A. A.; Ulm, E. H.; Vassil, T. C. J. Med. Chem. 1986, 29, 251-260. (e) Yanagisawa, H.; Ishihara, S.; Ando, A.; Kanazaki, T.; Miyamoto, S.; Koike, H.; Iijima, Y.; Oizumi, K.; Matsushita, Y.; Hata, T. J. Med. Chem. 1987, 30, 1984-1991. (f) Flynn, G. A.; Giroux, E. L.; Dage, R. C. J. Am. Chem. Soc. 1987, 109, 7914-7915. (g) Yanagisawa, H.; Ishihara, S.; Ando, A.; Kanazaki, T.; Miyamoto, S.; Koike, H.; Iijima, Y.; Oizumi, K.; Matsushita, Y.; Hata, T. J. Med. Chem. 1988, 31, 422-428. (h) Burkholder, T. P.; Huber, E. W.; Flynn, G. A. Bioorg. Med. Chem. Lett. 1992, 3, 231-234. (i) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Barown, B.; Ryono, D. E.; Bird, J. E.; Asaad, M. M.; Schaeffer, T. R.; Trippodo, N. C. J. Med. Chem. 1996, 39, 494-502.
14. In addition to monocyclic lactams of various ring sizes, the following list contains some lead references to derivatives of Freidinger lactams bearing heteroatom substituents. Selected references to related compounds containing additional cyclizations (fused or spiro) are included as well. (a) Thorsett, E. D.; Harris, E. E.; Aster, S.; Peterson, E. R; Taub, D.; Patchett, A. A. Biochem. Biophys, Res. Commun. 1983, 111, 166-171. (b) Thorsett, E. D.; Harris, E. E.; Aster, S. D.; Peterson, E. R.; Tristram, E. W.; Snyder, J. P.; Springer, J. P.; Patchett, A. A.; Ulm, E. H., In Peptides: Structure and Function; Hruby, V. J., Rich, D. H., Ed.; Pierce Chemical Co.: Rockford, IL, 1983; pp 555-558. (c) Watthey, J. W. H.; Stanton, J. L.; Desai, M.; Babiarz, J. E.; Finn, B. M. J. Med. Chem. 1985, 28, 1511-1516. (d) Thorsett, E. D.; Harris, E. E.; Aster, S. D.; Peterson, E. R.; Snyder, J. P.; Springer, J. P.; Hirshfield, J.; Tristram, E. W.; Patchett, A. A.; Ulm, E. H.; Vassil, T. C. J. Med. Chem. 1986, 29, 251-260. (e) Yanagisawa, H.; Ishihara, S.; Ando, A.; Kanazaki, T.; Miyamoto, S.; Koike, H.; Iijima, Y.; Oizumi, K.; Matsushita, Y.; Hata, T. J. Med. Chem. 1987, 30, 1984-1991. (f) Flynn, G. A.; Giroux, E. L.; Dage, R. C. J. Am. Chem. Soc. 1987, 109, 7914-7915. (g) Yanagisawa, H.; Ishihara, S.; Ando, A.; Kanazaki, T.; Miyamoto, S.; Koike, H.; Iijima, Y.; Oizumi, K.; Matsushita, Y.; Hata, T. J. Med. Chem. 1988, 31, 422-428. (h) Burkholder, T. P.; Huber, E. W.; Flynn, G. A. Bioorg. Med. Chem. Lett. 1992, 3, 231-234. (i) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Barown, B.; Ryono, D. E.; Bird, J. E.; Asaad, M. M.; Schaeffer, T. R.; Trippodo, N. C. J. Med. Chem. 1996, 39, 494-502.
15. In addition to monocyclic lactams of various ring sizes, the following list contains some lead references to derivatives of Freidinger lactams bearing heteroatom substituents. Selected references to related compounds containing additional cyclizations (fused or spiro) are included as well. (a) Thorsett, E. D.; Harris, E. E.; Aster, S.; Peterson, E. R; Taub, D.; Patchett, A. A. Biochem. Biophys, Res. Commun. 1983, 111, 166-171. (b) Thorsett, E. D.; Harris, E. E.; Aster, S. D.; Peterson, E. R.; Tristram, E. W.; Snyder, J. P.; Springer, J. P.; Patchett, A. A.; Ulm, E. H., In Peptides: Structure and Function; Hruby, V. J., Rich, D. H., Ed.; Pierce Chemical Co.: Rockford, IL, 1983; pp 555-558. (c) Watthey, J. W. H.; Stanton, J. L.; Desai, M.; Babiarz, J. E.; Finn, B. M. J. Med. Chem. 1985, 28, 1511-1516. (d) Thorsett, E. D.; Harris, E. E.; Aster, S. D.; Peterson, E. R.; Snyder, J. P.; Springer, J. P.; Hirshfield, J.; Tristram, E. W.; Patchett, A. A.; Ulm, E. H.; Vassil, T. C. J. Med. Chem. 1986, 29, 251-260. (e) Yanagisawa, H.; Ishihara, S.; Ando, A.; Kanazaki, T.; Miyamoto, S.; Koike, H.; Iijima, Y.; Oizumi, K.; Matsushita, Y.; Hata, T. J. Med. Chem. 1987, 30, 1984-1991. (f) Flynn, G. A.; Giroux, E. L.; Dage, R. C. J. Am. Chem. Soc. 1987, 109, 7914-7915. (g) Yanagisawa, H.; Ishihara, S.; Ando, A.; Kanazaki, T.; Miyamoto, S.; Koike, H.; Iijima, Y.; Oizumi, K.; Matsushita, Y.; Hata, T. J. Med. Chem. 1988, 31, 422-428. (h) Burkholder, T. P.; Huber, E. W.; Flynn, G. A. Bioorg. Med. Chem. Lett. 1992, 3, 231-234. (i) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Barown, B.; Ryono, D. E.; Bird, J. E.; Asaad, M. M.; Schaeffer, T. R.; Trippodo, N. C. J. Med. Chem. 1996, 39, 494-502.
16. In addition to monocyclic lactams of various ring sizes, the following list contains some lead references to derivatives of Freidinger lactams bearing heteroatom substituents. Selected references to related compounds containing additional cyclizations (fused or spiro) are included as well. (a) Thorsett, E. D.; Harris, E. E.; Aster, S.; Peterson, E. R; Taub, D.; Patchett, A. A. Biochem. Biophys, Res. Commun. 1983, 111, 166-171. (b) Thorsett, E. D.; Harris, E. E.; Aster, S. D.; Peterson, E. R.; Tristram, E. W.; Snyder, J. P.; Springer, J. P.; Patchett, A. A.; Ulm, E. H., In Peptides: Structure and Function; Hruby, V. J., Rich, D. H., Ed.; Pierce Chemical Co.: Rockford, IL, 1983; pp 555-558. (c) Watthey, J. W. H.; Stanton, J. L.; Desai, M.; Babiarz, J. E.; Finn, B. M. J. Med. Chem. 1985, 28, 1511-1516. (d) Thorsett, E. D.; Harris, E. E.; Aster, S. D.; Peterson, E. R.; Snyder, J. P.; Springer, J. P.; Hirshfield, J.; Tristram, E. W.; Patchett, A. A.; Ulm, E. H.; Vassil, T. C. J. Med. Chem. 1986, 29, 251-260. (e) Yanagisawa, H.; Ishihara, S.; Ando, A.; Kanazaki, T.; Miyamoto, S.; Koike, H.; Iijima, Y.; Oizumi, K.; Matsushita, Y.; Hata, T. J. Med. Chem. 1987, 30, 1984-1991. (f) Flynn, G. A.; Giroux, E. L.; Dage, R. C. J. Am. Chem. Soc. 1987, 109, 7914-7915. (g) Yanagisawa, H.; Ishihara, S.; Ando, A.; Kanazaki, T.; Miyamoto, S.; Koike, H.; Iijima, Y.; Oizumi, K.; Matsushita, Y.; Hata, T. J. Med. Chem. 1988, 31, 422-428. (h) Burkholder, T. P.; Huber, E. W.; Flynn, G. A. Bioorg. Med. Chem. Lett. 1992, 3, 231-234. (i) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Barown, B.; Ryono, D. E.; Bird, J. E.; Asaad, M. M.; Schaeffer, T. R.; Trippodo, N. C. J. Med. Chem. 1996, 39, 494-502.
17. In addition to monocyclic lactams of various ring sizes, the following list contains some lead references to derivatives of Freidinger lactams bearing heteroatom substituents. Selected references to related compounds containing additional cyclizations (fused or spiro) are included as well. (a) Thorsett, E. D.; Harris, E. E.; Aster, S.; Peterson, E. R; Taub, D.; Patchett, A. A. Biochem. Biophys, Res. Commun. 1983, 111, 166-171. (b) Thorsett, E. D.; Harris, E. E.; Aster, S. D.; Peterson, E. R.; Tristram, E. W.; Snyder, J. P.; Springer, J. P.; Patchett, A. A.; Ulm, E. H., In Peptides: Structure and Function; Hruby, V. J., Rich, D. H., Ed.; Pierce Chemical Co.: Rockford, IL, 1983; pp 555-558. (c) Watthey, J. W. H.; Stanton, J. L.; Desai, M.; Babiarz, J. E.; Finn, B. M. J. Med. Chem. 1985, 28, 1511-1516. (d) Thorsett, E. D.; Harris, E. E.; Aster, S. D.; Peterson, E. R.; Snyder, J. P.; Springer, J. P.; Hirshfield, J.; Tristram, E. W.; Patchett, A. A.; Ulm, E. H.; Vassil, T. C. J. Med. Chem. 1986, 29, 251-260. (e) Yanagisawa, H.; Ishihara, S.; Ando, A.; Kanazaki, T.; Miyamoto, S.; Koike, H.; Iijima, Y.; Oizumi, K.; Matsushita, Y.; Hata, T. J. Med. Chem. 1987, 30, 1984-1991. (f) Flynn, G. A.; Giroux, E. L.; Dage, R. C. J. Am. Chem. Soc. 1987, 109, 7914-7915. (g) Yanagisawa, H.; Ishihara, S.; Ando, A.; Kanazaki, T.; Miyamoto, S.; Koike, H.; Iijima, Y.; Oizumi, K.; Matsushita, Y.; Hata, T. J. Med. Chem. 1988, 31, 422-428. (h) Burkholder, T. P.; Huber, E. W.; Flynn, G. A. Bioorg. Med. Chem. Lett. 1992, 3, 231-234. (i) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Barown, B.; Ryono, D. E.; Bird, J. E.; Asaad, M. M.; Schaeffer, T. R.; Trippodo, N. C. J. Med. Chem. 1996, 39, 494-502.
18. In addition to monocyclic lactams of various ring sizes, the following list contains some lead references to derivatives of Freidinger lactams bearing heteroatom substituents. Selected references to related compounds containing additional cyclizations (fused or spiro) are included as well. (a) Thorsett, E. D.; Harris, E. E.; Aster, S.; Peterson, E. R; Taub, D.; Patchett, A. A. Biochem. Biophys, Res. Commun. 1983, 111, 166-171. (b) Thorsett, E. D.; Harris, E. E.; Aster, S. D.; Peterson, E. R.; Tristram, E. W.; Snyder, J. P.; Springer, J. P.; Patchett, A. A.; Ulm, E. H., In Peptides: Structure and Function; Hruby, V. J., Rich, D. H., Ed.; Pierce Chemical Co.: Rockford, IL, 1983; pp 555-558. (c) Watthey, J. W. H.; Stanton, J. L.; Desai, M.; Babiarz, J. E.; Finn, B. M. J. Med. Chem. 1985, 28, 1511-1516. (d) Thorsett, E. D.; Harris, E. E.; Aster, S. D.; Peterson, E. R.; Snyder, J. P.; Springer, J. P.; Hirshfield, J.; Tristram, E. W.; Patchett, A. A.; Ulm, E. H.; Vassil, T. C. J. Med. Chem. 1986, 29, 251-260. (e) Yanagisawa, H.; Ishihara, S.; Ando, A.; Kanazaki, T.; Miyamoto, S.; Koike, H.; Iijima, Y.; Oizumi, K.; Matsushita, Y.; Hata, T. J. Med. Chem. 1987, 30, 1984-1991. (f) Flynn, G. A.; Giroux, E. L.; Dage, R. C. J. Am. Chem. Soc. 1987, 109, 7914-7915. (g) Yanagisawa, H.; Ishihara, S.; Ando, A.; Kanazaki, T.; Miyamoto, S.; Koike, H.; Iijima, Y.; Oizumi, K.; Matsushita, Y.; Hata, T. J. Med. Chem. 1988, 31, 422-428. (h) Burkholder, T. P.; Huber, E. W.; Flynn, G. A. Bioorg. Med. Chem. Lett. 1992, 3, 231-234. (i) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Barown, B.; Ryono, D. E.; Bird, J. E.; Asaad, M. M.; Schaeffer, T. R.; Trippodo, N. C. J. Med. Chem. 1996, 39, 494-502.
19. In addition to monocyclic lactams of various ring sizes, the following list contains some lead references to derivatives of Freidinger lactams bearing heteroatom substituents. Selected references to related compounds containing additional cyclizations (fused or spiro) are included as well. (a) Thorsett, E. D.; Harris, E. E.; Aster, S.; Peterson, E. R; Taub, D.; Patchett, A. A. Biochem. Biophys, Res. Commun. 1983, 111, 166-171. (b) Thorsett, E. D.; Harris, E. E.; Aster, S. D.; Peterson, E. R.; Tristram, E. W.; Snyder, J. P.; Springer, J. P.; Patchett, A. A.; Ulm, E. H., In Peptides: Structure and Function; Hruby, V. J., Rich, D. H., Ed.; Pierce Chemical Co.: Rockford, IL, 1983; pp 555-558. (c) Watthey, J. W. H.; Stanton, J. L.; Desai, M.; Babiarz, J. E.; Finn, B. M. J. Med. Chem. 1985, 28, 1511-1516. (d) Thorsett, E. D.; Harris, E. E.; Aster, S. D.; Peterson, E. R.; Snyder, J. P.; Springer, J. P.; Hirshfield, J.; Tristram, E. W.; Patchett, A. A.; Ulm, E. H.; Vassil, T. C. J. Med. Chem. 1986, 29, 251-260. (e) Yanagisawa, H.; Ishihara, S.; Ando, A.; Kanazaki, T.; Miyamoto, S.; Koike, H.; Iijima, Y.; Oizumi, K.; Matsushita, Y.; Hata, T. J. Med. Chem. 1987, 30, 1984-1991. (f) Flynn, G. A.; Giroux, E. L.; Dage, R. C. J. Am. Chem. Soc. 1987, 109, 7914-7915. (g) Yanagisawa, H.; Ishihara, S.; Ando, A.; Kanazaki, T.; Miyamoto, S.; Koike, H.; Iijima, Y.; Oizumi, K.; Matsushita, Y.; Hata, T. J. Med. Chem. 1988, 31, 422-428. (h) Burkholder, T. P.; Huber, E. W.; Flynn, G. A. Bioorg. Med. Chem. Lett. 1992, 3, 231-234. (i) Robl, J. A.; Cimarusti, M. P.; Simpkins, L. M.; Barown, B.; Ryono, D. E.; Bird, J. E.; Asaad, M. M.; Schaeffer, T. R.; Trippodo, N. C. J. Med. Chem. 1996, 39, 494-502.
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32. 9 However, the preference for like stereochemistry using phenylalanine methyl ester (Phe-OMe) is probably a consequence of the rules for prioritizing substituents in the Cahn-Prelog-Ingold system; hence, L-Phe-OMe (i.e., (S)-Phe-OMe) can be super-imposed onto (-R)-α-methylbenzylamine better than it can be super-imposed onto (S)-α-methylbenzylamine (see structures below). The use of either of these two amines results in a preference for S stereochemistry at N-2 of the resulting oxaziridine.
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41. 218 = 23 nM).
42. 218 = 23 nM).