Effective tuning of the arene and alkanesulfinamides for highly enantioselective synthesis of (S)-4-chlorophenylphenylmethylamine, a key intermediate for antihistamic (S)-cetirizine

Tetrahedron Letters

Volumn 44, Issue 22, 2003, Pages 4195-4197

  Han, Zhengxu ^a   Krishnamurthy, Dhileepkumar ^a,b   Grover, Paul ^a   Fang, Q Kevin ^a   Pflum, Derek A ^a   Senanayake, Chris H ^a,b  

^a SUNOVION PHARMACEUTICALS INC   (United States)

^b BOEHRINGER INGELHEIM PHARMACEUTICALS INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

4 CHLOROPHENYLPHENYLMETHYLAMINE; ALKANE DERIVATIVE; ANTIHISTAMINIC AGENT; BROMINE DERIVATIVE; CETIRIZINE; IMINE; POLYCYCLIC AROMATIC HYDROCARBON; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SULFINAMIDE; UNCLASSIFIED DRUG;

ARTICLE; DIASTEREOISOMER; DRUG SYNTHESIS; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOCHEMISTRY;

ARENE;

EID: 0037725132     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00903-1     Document Type: Article

References (32)

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15. For the use of Ellman's tert-butanesulfinamide as auxiliary in the synthesis of chiral nitrogen containing compounds, see: (a) Owens, D. T.; Hollander, J. F.; Oliver, A. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 1539 and references cited therein; (b) Liu, G.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913; (c) Cogan, D. A.; Liu, G.; Ellman, J. A. Tetrahedron Lett. 1999, 40, 6709; (d) Davis, F. A.; McCoull, W. J. Org. Chem. 1999, 64, 3396; (e) Tang, T. P.; Volkman, S. K.; Ellman, J. A. J. Org. Chem. 2001, 66, 8772; (f) Lee, Y.; Silverman, R. B. Org. Lett. 2000, 2, 303; (g) Borg, G.; Chino, M.; Elmann, J. A. Tetrahedron Lett. 2001, 42, 1433; (h) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847; (i) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Angew. Chem., Int. Ed. 2001, 40, 589; (j) Lee, A.; Elman, J. A. Org. Lett. 2001, 3, 3707; (k) Barrow, J. C.; Ngo, P. L.; Pellicore, J. M.; Selnick, H. G.; Nantermet, P. G. Tetrahedron Lett. 2001, 42, 2051.
16. For the use of Ellman's tert-butanesulfinamide as auxiliary in the synthesis of chiral nitrogen containing compounds, see: (a) Owens, D. T.; Hollander, J. F.; Oliver, A. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 1539 and references cited therein; (b) Liu, G.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913; (c) Cogan, D. A.; Liu, G.; Ellman, J. A. Tetrahedron Lett. 1999, 40, 6709; (d) Davis, F. A.; McCoull, W. J. Org. Chem. 1999, 64, 3396; (e) Tang, T. P.; Volkman, S. K.; Ellman, J. A. J. Org. Chem. 2001, 66, 8772; (f) Lee, Y.; Silverman, R. B. Org. Lett. 2000, 2, 303; (g) Borg, G.; Chino, M.; Elmann, J. A. Tetrahedron Lett. 2001, 42, 1433; (h) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847; (i) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Angew. Chem., Int. Ed. 2001, 40, 589; (j) Lee, A.; Elman, J. A. Org. Lett. 2001, 3, 3707; (k) Barrow, J. C.; Ngo, P. L.; Pellicore, J. M.; Selnick, H. G.; Nantermet, P. G. Tetrahedron Lett. 2001, 42, 2051.
17. For the use of Ellman's tert-butanesulfinamide as auxiliary in the synthesis of chiral nitrogen containing compounds, see: (a) Owens, D. T.; Hollander, J. F.; Oliver, A. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 1539 and references cited therein; (b) Liu, G.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913; (c) Cogan, D. A.; Liu, G.; Ellman, J. A. Tetrahedron Lett. 1999, 40, 6709; (d) Davis, F. A.; McCoull, W. J. Org. Chem. 1999, 64, 3396; (e) Tang, T. P.; Volkman, S. K.; Ellman, J. A. J. Org. Chem. 2001, 66, 8772; (f) Lee, Y.; Silverman, R. B. Org. Lett. 2000, 2, 303; (g) Borg, G.; Chino, M.; Elmann, J. A. Tetrahedron Lett. 2001, 42, 1433; (h) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847; (i) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Angew. Chem., Int. Ed. 2001, 40, 589; (j) Lee, A.; Elman, J. A. Org. Lett. 2001, 3, 3707; (k) Barrow, J. C.; Ngo, P. L.; Pellicore, J. M.; Selnick, H. G.; Nantermet, P. G. Tetrahedron Lett. 2001, 42, 2051.
18. For the use of Ellman's tert-butanesulfinamide as auxiliary in the synthesis of chiral nitrogen containing compounds, see: (a) Owens, D. T.; Hollander, J. F.; Oliver, A. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 1539 and references cited therein; (b) Liu, G.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913; (c) Cogan, D. A.; Liu, G.; Ellman, J. A. Tetrahedron Lett. 1999, 40, 6709; (d) Davis, F. A.; McCoull, W. J. Org. Chem. 1999, 64, 3396; (e) Tang, T. P.; Volkman, S. K.; Ellman, J. A. J. Org. Chem. 2001, 66, 8772; (f) Lee, Y.; Silverman, R. B. Org. Lett. 2000, 2, 303; (g) Borg, G.; Chino, M.; Elmann, J. A. Tetrahedron Lett. 2001, 42, 1433; (h) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847; (i) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Angew. Chem., Int. Ed. 2001, 40, 589; (j) Lee, A.; Elman, J. A. Org. Lett. 2001, 3, 3707; (k) Barrow, J. C.; Ngo, P. L.; Pellicore, J. M.; Selnick, H. G.; Nantermet, P. G. Tetrahedron Lett. 2001, 42, 2051.
19. For the use of Ellman's tert-butanesulfinamide as auxiliary in the synthesis of chiral nitrogen containing compounds, see: (a) Owens, D. T.; Hollander, J. F.; Oliver, A. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 1539 and references cited therein; (b) Liu, G.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913; (c) Cogan, D. A.; Liu, G.; Ellman, J. A. Tetrahedron Lett. 1999, 40, 6709; (d) Davis, F. A.; McCoull, W. J. Org. Chem. 1999, 64, 3396; (e) Tang, T. P.; Volkman, S. K.; Ellman, J. A. J. Org. Chem. 2001, 66, 8772; (f) Lee, Y.; Silverman, R. B. Org. Lett. 2000, 2, 303; (g) Borg, G.; Chino, M.; Elmann, J. A. Tetrahedron Lett. 2001, 42, 1433; (h) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847; (i) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Angew. Chem., Int. Ed. 2001, 40, 589; (j) Lee, A.; Elman, J. A. Org. Lett. 2001, 3, 3707; (k) Barrow, J. C.; Ngo, P. L.; Pellicore, J. M.; Selnick, H. G.; Nantermet, P. G. Tetrahedron Lett. 2001, 42, 2051.
20. For the use of Ellman's tert-butanesulfinamide as auxiliary in the synthesis of chiral nitrogen containing compounds, see: (a) Owens, D. T.; Hollander, J. F.; Oliver, A. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 1539 and references cited therein; (b) Liu, G.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913; (c) Cogan, D. A.; Liu, G.; Ellman, J. A. Tetrahedron Lett. 1999, 40, 6709; (d) Davis, F. A.; McCoull, W. J. Org. Chem. 1999, 64, 3396; (e) Tang, T. P.; Volkman, S. K.; Ellman, J. A. J. Org. Chem. 2001, 66, 8772; (f) Lee, Y.; Silverman, R. B. Org. Lett. 2000, 2, 303; (g) Borg, G.; Chino, M.; Elmann, J. A. Tetrahedron Lett. 2001, 42, 1433; (h) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847; (i) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Angew. Chem., Int. Ed. 2001, 40, 589; (j) Lee, A.; Elman, J. A. Org. Lett. 2001, 3, 3707; (k) Barrow, J. C.; Ngo, P. L.; Pellicore, J. M.; Selnick, H. G.; Nantermet, P. G. Tetrahedron Lett. 2001, 42, 2051.
21. For the use of Ellman's tert-butanesulfinamide as auxiliary in the synthesis of chiral nitrogen containing compounds, see: (a) Owens, D. T.; Hollander, J. F.; Oliver, A. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 1539 and references cited therein; (b) Liu, G.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913; (c) Cogan, D. A.; Liu, G.; Ellman, J. A. Tetrahedron Lett. 1999, 40, 6709; (d) Davis, F. A.; McCoull, W. J. Org. Chem. 1999, 64, 3396; (e) Tang, T. P.; Volkman, S. K.; Ellman, J. A. J. Org. Chem. 2001, 66, 8772; (f) Lee, Y.; Silverman, R. B. Org. Lett. 2000, 2, 303; (g) Borg, G.; Chino, M.; Elmann, J. A. Tetrahedron Lett. 2001, 42, 1433; (h) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847; (i) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Angew. Chem., Int. Ed. 2001, 40, 589; (j) Lee, A.; Elman, J. A. Org. Lett. 2001, 3, 3707; (k) Barrow, J. C.; Ngo, P. L.; Pellicore, J. M.; Selnick, H. G.; Nantermet, P. G. Tetrahedron Lett. 2001, 42, 2051.
22. For the use of Ellman's tert-butanesulfinamide as auxiliary in the synthesis of chiral nitrogen containing compounds, see: (a) Owens, D. T.; Hollander, J. F.; Oliver, A. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 1539 and references cited therein; (b) Liu, G.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913; (c) Cogan, D. A.; Liu, G.; Ellman, J. A. Tetrahedron Lett. 1999, 40, 6709; (d) Davis, F. A.; McCoull, W. J. Org. Chem. 1999, 64, 3396; (e) Tang, T. P.; Volkman, S. K.; Ellman, J. A. J. Org. Chem. 2001, 66, 8772; (f) Lee, Y.; Silverman, R. B. Org. Lett. 2000, 2, 303; (g) Borg, G.; Chino, M.; Elmann, J. A. Tetrahedron Lett. 2001, 42, 1433; (h) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847; (i) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Angew. Chem., Int. Ed. 2001, 40, 589; (j) Lee, A.; Elman, J. A. Org. Lett. 2001, 3, 3707; (k) Barrow, J. C.; Ngo, P. L.; Pellicore, J. M.; Selnick, H. G.; Nantermet, P. G. Tetrahedron Lett. 2001, 42, 2051.
23. For the use of Ellman's tert-butanesulfinamide as auxiliary in the synthesis of chiral nitrogen containing compounds, see: (a) Owens, D. T.; Hollander, J. F.; Oliver, A. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 1539 and references cited therein; (b) Liu, G.; Cogan, D. A.; Ellman, J. A. J. Am. Chem. Soc. 1997, 119, 9913; (c) Cogan, D. A.; Liu, G.; Ellman, J. A. Tetrahedron Lett. 1999, 40, 6709; (d) Davis, F. A.; McCoull, W. J. Org. Chem. 1999, 64, 3396; (e) Tang, T. P.; Volkman, S. K.; Ellman, J. A. J. Org. Chem. 2001, 66, 8772; (f) Lee, Y.; Silverman, R. B. Org. Lett. 2000, 2, 303; (g) Borg, G.; Chino, M.; Elmann, J. A. Tetrahedron Lett. 2001, 42, 1433; (h) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Org. Lett. 2001, 3, 2847; (i) Prakash, G. K. S.; Mandal, M.; Olah, G. A. Angew. Chem., Int. Ed. 2001, 40, 589; (j) Lee, A.; Elman, J. A. Org. Lett. 2001, 3, 3707; (k) Barrow, J. C.; Ngo, P. L.; Pellicore, J. M.; Selnick, H. G.; Nantermet, P. G. Tetrahedron Lett. 2001, 42, 2051.
24. For the use of Davis' p-toluenesulfinamide as auxiliary in the synthesis of chiral nitrogen containing compounds, see: (a) Davis, F. A.; Reddy, R. E.; Szewezyk, J. M.; Portonovo, P. S. Tetrahedron Lett. 1993, 34, 6229; (b) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13; (c) Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555; (d) Zhou, P.; Chen, B.-C.; Davis, F. A. Advances in Sulfur Chemistry, Rayner, C. M., Ed.; JAL Press, 2000, Vol. 2, p. 249; (e) Davis, F. A.; Lee, S.; Zhang, H.; Fanelli, D. L. J. Org. Chem. 2000, 2, 8704.
25. For the use of Davis' p-toluenesulfinamide as auxiliary in the synthesis of chiral nitrogen containing compounds, see: (a) Davis, F. A.; Reddy, R. E.; Szewezyk, J. M.; Portonovo, P. S. Tetrahedron Lett. 1993, 34, 6229; (b) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13; (c) Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555; (d) Zhou, P.; Chen, B.-C.; Davis, F. A. Advances in Sulfur Chemistry, Rayner, C. M., Ed.; JAL Press, 2000, Vol. 2, p. 249; (e) Davis, F. A.; Lee, S.; Zhang, H.; Fanelli, D. L. J. Org. Chem. 2000, 2, 8704.
26. For the use of Davis' p-toluenesulfinamide as auxiliary in the synthesis of chiral nitrogen containing compounds, see: (a) Davis, F. A.; Reddy, R. E.; Szewezyk, J. M.; Portonovo, P. S. Tetrahedron Lett. 1993, 34, 6229; (b) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13; (c) Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555; (d) Zhou, P.; Chen, B.-C.; Davis, F. A. Advances in Sulfur Chemistry, Rayner, C. M., Ed.; JAL Press, 2000, Vol. 2, p. 249; (e) Davis, F. A.; Lee, S.; Zhang, H.; Fanelli, D. L. J. Org. Chem. 2000, 2, 8704.
27. For the use of Davis' p-toluenesulfinamide as auxiliary in the synthesis of chiral nitrogen containing compounds, see: (a) Davis, F. A.; Reddy, R. E.; Szewezyk, J. M.; Portonovo, P. S. Tetrahedron Lett. 1993, 34, 6229; (b) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13; (c) Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555; (d) Zhou, P.; Chen, B.-C.; Davis, F. A. Advances in Sulfur Chemistry, Rayner, C. M., Ed.; JAL Press, 2000, Vol. 2, p. 249; (e) Davis, F. A.; Lee, S.; Zhang, H.; Fanelli, D. L. J. Org. Chem. 2000, 2, 8704.
28. For the use of Davis' p-toluenesulfinamide as auxiliary in the synthesis of chiral nitrogen containing compounds, see: (a) Davis, F. A.; Reddy, R. E.; Szewezyk, J. M.; Portonovo, P. S. Tetrahedron Lett. 1993, 34, 6229; (b) Davis, F. A.; Zhou, P.; Chen, B.-C. Chem. Soc. Rev. 1998, 27, 13; (c) Davis, F. A.; Reddy, R. E.; Szewczyk, J. M.; Reddy, G. V.; Portonovo, P. S.; Zhang, H.; Fanelli, D.; Reddy, R. T.; Zhou, P.; Carroll, P. J. J. Org. Chem. 1997, 62, 2555; (d) Zhou, P.; Chen, B.-C.; Davis, F. A. Advances in Sulfur Chemistry, Rayner, C. M., Ed.; JAL Press, 2000, Vol. 2, p. 249; (e) Davis, F. A.; Lee, S.; Zhang, H.; Fanelli, D. L. J. Org. Chem. 2000, 2, 8704.
29. For the first evaluation of the effect of the structure of chiral sulfinamides in asymmetric synthesis of chiral amines, see: Han Z., Krishnamurthy D., Pflum D., Grover P., Wald S.A., Senanayake C.H. Org. Lett. 4:2002;4025.
30. Han Z., Krishnamurthy D., Grover P., Fang K.Q., Senanayake C.H. J. Am. Chem. Soc. 124:2002;7880.
31. 3): 23.9, 24.3, 24.5, 28.4, 34.4, 123.1, 138.9, 147.9, 152.0.
32. 3.