Enantioselective protonation of prochiral enolates in the asymmetric synthesis of (S)-naproxen

Tetrahedron Letters

Volumn 44, Issue 10, 2003, Pages 2023-2026

  Muñoz Muñiz, Omar ^a   Juaristi, Eusebio ^a  

^a DEPARTAMENTO DE FÍSICA   (Mexico)

Author keywords

Chiral acids; Enantioselective protonations; Enolate desymmetrization; Naproxen; Prochiral enolates; Resolution of racemates

Indexed keywords

ALPHA METHYLBENZYLAMINE; ESTER DERIVATIVE; NAPROXEN;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; ENANTIOSELECTIVITY; PROTON TRANSPORT; SAPONIFICATION;

EID: 0037416856     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)00217-X     Document Type: Article

References (49)

1. Eliel E.L., Koskimies J.K., Lohri B., Frazee W.J., Morris-Natschke S., Lynch J.E., Soai K. Eliel E.L., Otsuka S. Asymmetric Reactions and Processes. 1982;American Chemical Society, Washington, Evans, D. A. In Asymmetric Synthesis; Morrison, J. D.; Academic Press: New York, 1983-1984; Vol. 3, pp. 1-110.
2. Seebach D., Juaristi E., Miller D.D., Schickli C., Weber T. Helv. Chim. Acta. 70:1987;237.
3. Enders D., Bettray W., Raabe G., Runsink J. Synthesis. 1994;1322. and references cited therein.
4. Oppolzer W. Pure Appl. Chem. 62:1990;1241.
5. Seyden-Penne J. Chiral Auxiliaries and Ligands in Asymmetric Synthesis. 1995;Wiley, New York.
6. Juaristi E., Quintana D., Balderas M., García-Pérez E. Tetrahedron: Asymmetry. 7:1996;2233.
7. León-Romo J.L., Virues C.I., Aviña J., Regla I., Juaristi E. Chirality. 14:2002;144.
8. Basic concepts, see for example: (a) Juaristi, E. Introduction to Stereochemistry and Conformational Analysis; Wiley: New York, 1991; (b) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994; (c) Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624; (d) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271.
9. Basic concepts, see for example: (a) Juaristi, E. Introduction to Stereochemistry and Conformational Analysis; Wiley: New York, 1991; (b) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994; (c) Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624; (d) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271.
10. Basic concepts, see for example: (a) Juaristi, E. Introduction to Stereochemistry and Conformational Analysis; Wiley: New York, 1991; (b) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994; (c) Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624; (d) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271.
11. Basic concepts, see for example: (a) Juaristi, E. Introduction to Stereochemistry and Conformational Analysis; Wiley: New York, 1991; (b) Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley: New York, 1994; (c) Seebach, D. Angew. Chem., Int. Ed. Engl. 1988, 27, 1624; (d) Juaristi, E.; Beck, A. K.; Hansen, J.; Matt, T.; Mukhopadhyay, T.; Simson, M.; Seebach, D. Synthesis 1993, 1271.
12. Pioneering work: (a) Duhamel, L.; Plaquevent, J. C. J. Am. Chem. Soc. 1978, 100, 7415; (b) Duhamel, L.; Duhamel, P.; Launay, J.-C.; Plaquevent, J.-C. Bull. Soc. Chim. Fr. 1984, 421; (c) Fehr, C.; Galindo, J. J. Am. Chem. Soc. 1988, 110, 6909; (d) Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566.
13. Pioneering work: (a) Duhamel, L.; Plaquevent, J. C. J. Am. Chem. Soc. 1978, 100, 7415; (b) Duhamel, L.; Duhamel, P.; Launay, J.-C.; Plaquevent, J.-C. Bull. Soc. Chim. Fr. 1984, 421; (c) Fehr, C.; Galindo, J. J. Am. Chem. Soc. 1988, 110, 6909; (d) Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566.
14. Pioneering work: (a) Duhamel, L.; Plaquevent, J. C. J. Am. Chem. Soc. 1978, 100, 7415; (b) Duhamel, L.; Duhamel, P.; Launay, J.-C.; Plaquevent, J.-C. Bull. Soc. Chim. Fr. 1984, 421; (c) Fehr, C.; Galindo, J. J. Am. Chem. Soc. 1988, 110, 6909; (d) Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566.
15. Pioneering work: (a) Duhamel, L.; Plaquevent, J. C. J. Am. Chem. Soc. 1978, 100, 7415; (b) Duhamel, L.; Duhamel, P.; Launay, J.-C.; Plaquevent, J.-C. Bull. Soc. Chim. Fr. 1984, 421; (c) Fehr, C.; Galindo, J. J. Am. Chem. Soc. 1988, 110, 6909; (d) Fehr, C. Angew. Chem., Int. Ed. Engl. 1996, 35, 2566.
16. Mechanistic studies: (a) Vedejs, E.; Lee, N.; Sakata, S. T. J. Am. Chem. Soc. 1994, 116, 2175; (b) Vedejs, E.; Kruger, A. W.; Suna, E. J. Org. Chem. 1999, 64, 7863; (c) Vedejs, E.; Kruger, A. W.; Lee, N.; Sakata, T.; Stec, M.; Suna, E. J. Am. Chem. Soc. 2000, 122, 4602.
17. Mechanistic studies: (a) Vedejs, E.; Lee, N.; Sakata, S. T. J. Am. Chem. Soc. 1994, 116, 2175; (b) Vedejs, E.; Kruger, A. W.; Suna, E. J. Org. Chem. 1999, 64, 7863; (c) Vedejs, E.; Kruger, A. W.; Lee, N.; Sakata, T.; Stec, M.; Suna, E. J. Am. Chem. Soc. 2000, 122, 4602.
18. Mechanistic studies: (a) Vedejs, E.; Lee, N.; Sakata, S. T. J. Am. Chem. Soc. 1994, 116, 2175; (b) Vedejs, E.; Kruger, A. W.; Suna, E. J. Org. Chem. 1999, 64, 7863; (c) Vedejs, E.; Kruger, A. W.; Lee, N.; Sakata, T.; Stec, M.; Suna, E. J. Am. Chem. Soc. 2000, 122, 4602.
19. Salient examples: (a) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854; (b) Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861; (c) Asensio, G.; Aleman, P.; Gil, J.; Dommingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342; (d) Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Yamamoto, H. J. Org. Chem. 2000, 65, 2979; (e) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691; (f) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847; (g) Matsumoto, K.; Tsutsumi, S.; Ihori, T.; Ohta, H. J. Am. Chem. Soc. 1990, 112, 9614; (h) Fujii, I.; Lerner, R. A.; Janda, K. D. J. Am. Chem. Soc. 1991, 113, 8528; (i) Potin, D.; Williams, K.; Rebek, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 1420; (j) Roy, O.; Riahi, A.; Hénin, F.; Muzart, J. Eur. J. Org. Chem. 2002, 3986; (k) Landais, Y.; Zekri, E. Eur. J. Org. Chem. 2002, 4037.
20. Salient examples: (a) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854; (b) Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861; (c) Asensio, G.; Aleman, P.; Gil, J.; Dommingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342; (d) Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Yamamoto, H. J. Org. Chem. 2000, 65, 2979; (e) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691; (f) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847; (g) Matsumoto, K.; Tsutsumi, S.; Ihori, T.; Ohta, H. J. Am. Chem. Soc. 1990, 112, 9614; (h) Fujii, I.; Lerner, R. A.; Janda, K. D. J. Am. Chem. Soc. 1991, 113, 8528; (i) Potin, D.; Williams, K.; Rebek, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 1420; (j) Roy, O.; Riahi, A.; Hénin, F.; Muzart, J. Eur. J. Org. Chem. 2002, 3986; (k) Landais, Y.; Zekri, E. Eur. J. Org. Chem. 2002, 4037.
21. Salient examples: (a) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854; (b) Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861; (c) Asensio, G.; Aleman, P.; Gil, J.; Dommingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342; (d) Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Yamamoto, H. J. Org. Chem. 2000, 65, 2979; (e) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691; (f) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847; (g) Matsumoto, K.; Tsutsumi, S.; Ihori, T.; Ohta, H. J. Am. Chem. Soc. 1990, 112, 9614; (h) Fujii, I.; Lerner, R. A.; Janda, K. D. J. Am. Chem. Soc. 1991, 113, 8528; (i) Potin, D.; Williams, K.; Rebek, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 1420; (j) Roy, O.; Riahi, A.; Hénin, F.; Muzart, J. Eur. J. Org. Chem. 2002, 3986; (k) Landais, Y.; Zekri, E. Eur. J. Org. Chem. 2002, 4037.
22. Salient examples: (a) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854; (b) Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861; (c) Asensio, G.; Aleman, P.; Gil, J.; Dommingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342; (d) Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Yamamoto, H. J. Org. Chem. 2000, 65, 2979; (e) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691; (f) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847; (g) Matsumoto, K.; Tsutsumi, S.; Ihori, T.; Ohta, H. J. Am. Chem. Soc. 1990, 112, 9614; (h) Fujii, I.; Lerner, R. A.; Janda, K. D. J. Am. Chem. Soc. 1991, 113, 8528; (i) Potin, D.; Williams, K.; Rebek, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 1420; (j) Roy, O.; Riahi, A.; Hénin, F.; Muzart, J. Eur. J. Org. Chem. 2002, 3986; (k) Landais, Y.; Zekri, E. Eur. J. Org. Chem. 2002, 4037.
23. Salient examples: (a) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854; (b) Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861; (c) Asensio, G.; Aleman, P.; Gil, J.; Dommingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342; (d) Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Yamamoto, H. J. Org. Chem. 2000, 65, 2979; (e) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691; (f) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847; (g) Matsumoto, K.; Tsutsumi, S.; Ihori, T.; Ohta, H. J. Am. Chem. Soc. 1990, 112, 9614; (h) Fujii, I.; Lerner, R. A.; Janda, K. D. J. Am. Chem. Soc. 1991, 113, 8528; (i) Potin, D.; Williams, K.; Rebek, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 1420; (j) Roy, O.; Riahi, A.; Hénin, F.; Muzart, J. Eur. J. Org. Chem. 2002, 3986; (k) Landais, Y.; Zekri, E. Eur. J. Org. Chem. 2002, 4037.
24. Salient examples: (a) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854; (b) Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861; (c) Asensio, G.; Aleman, P.; Gil, J.; Dommingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342; (d) Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Yamamoto, H. J. Org. Chem. 2000, 65, 2979; (e) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691; (f) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847; (g) Matsumoto, K.; Tsutsumi, S.; Ihori, T.; Ohta, H. J. Am. Chem. Soc. 1990, 112, 9614; (h) Fujii, I.; Lerner, R. A.; Janda, K. D. J. Am. Chem. Soc. 1991, 113, 8528; (i) Potin, D.; Williams, K.; Rebek, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 1420; (j) Roy, O.; Riahi, A.; Hénin, F.; Muzart, J. Eur. J. Org. Chem. 2002, 3986; (k) Landais, Y.; Zekri, E. Eur. J. Org. Chem. 2002, 4037.
25. Salient examples: (a) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854; (b) Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861; (c) Asensio, G.; Aleman, P.; Gil, J.; Dommingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342; (d) Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Yamamoto, H. J. Org. Chem. 2000, 65, 2979; (e) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691; (f) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847; (g) Matsumoto, K.; Tsutsumi, S.; Ihori, T.; Ohta, H. J. Am. Chem. Soc. 1990, 112, 9614; (h) Fujii, I.; Lerner, R. A.; Janda, K. D. J. Am. Chem. Soc. 1991, 113, 8528; (i) Potin, D.; Williams, K.; Rebek, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 1420; (j) Roy, O.; Riahi, A.; Hénin, F.; Muzart, J. Eur. J. Org. Chem. 2002, 3986; (k) Landais, Y.; Zekri, E. Eur. J. Org. Chem. 2002, 4037.
26. Salient examples: (a) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854; (b) Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861; (c) Asensio, G.; Aleman, P.; Gil, J.; Dommingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342; (d) Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Yamamoto, H. J. Org. Chem. 2000, 65, 2979; (e) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691; (f) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847; (g) Matsumoto, K.; Tsutsumi, S.; Ihori, T.; Ohta, H. J. Am. Chem. Soc. 1990, 112, 9614; (h) Fujii, I.; Lerner, R. A.; Janda, K. D. J. Am. Chem. Soc. 1991, 113, 8528; (i) Potin, D.; Williams, K.; Rebek, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 1420; (j) Roy, O.; Riahi, A.; Hénin, F.; Muzart, J. Eur. J. Org. Chem. 2002, 3986; (k) Landais, Y.; Zekri, E. Eur. J. Org. Chem. 2002, 4037.
27. Salient examples: (a) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854; (b) Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861; (c) Asensio, G.; Aleman, P.; Gil, J.; Dommingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342; (d) Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Yamamoto, H. J. Org. Chem. 2000, 65, 2979; (e) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691; (f) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847; (g) Matsumoto, K.; Tsutsumi, S.; Ihori, T.; Ohta, H. J. Am. Chem. Soc. 1990, 112, 9614; (h) Fujii, I.; Lerner, R. A.; Janda, K. D. J. Am. Chem. Soc. 1991, 113, 8528; (i) Potin, D.; Williams, K.; Rebek, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 1420; (j) Roy, O.; Riahi, A.; Hénin, F.; Muzart, J. Eur. J. Org. Chem. 2002, 3986; (k) Landais, Y.; Zekri, E. Eur. J. Org. Chem. 2002, 4037.
28. Salient examples: (a) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854; (b) Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861; (c) Asensio, G.; Aleman, P.; Gil, J.; Dommingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342; (d) Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Yamamoto, H. J. Org. Chem. 2000, 65, 2979; (e) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691; (f) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847; (g) Matsumoto, K.; Tsutsumi, S.; Ihori, T.; Ohta, H. J. Am. Chem. Soc. 1990, 112, 9614; (h) Fujii, I.; Lerner, R. A.; Janda, K. D. J. Am. Chem. Soc. 1991, 113, 8528; (i) Potin, D.; Williams, K.; Rebek, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 1420; (j) Roy, O.; Riahi, A.; Hénin, F.; Muzart, J. Eur. J. Org. Chem. 2002, 3986; (k) Landais, Y.; Zekri, E. Eur. J. Org. Chem. 2002, 4037.
29. Salient examples: (a) Ishihara, K.; Nakamura, S.; Kaneeda, M.; Yamamoto, H. J. Am. Chem. Soc. 1996, 118, 12854; (b) Kosugi, H.; Hoshino, K.; Uda, H. Tetrahedron Lett. 1997, 38, 6861; (c) Asensio, G.; Aleman, P.; Gil, J.; Dommingo, L. R.; Medio-Simon, M. J. Org. Chem. 1998, 63, 9342; (d) Yanagisawa, A.; Watanabe, T.; Kikuchi, T.; Yamamoto, H. J. Org. Chem. 2000, 65, 2979; (e) Takeuchi, S.; Nakamura, Y.; Ohgo, Y.; Curran, D. P. Tetrahedron Lett. 1998, 39, 8691; (f) Aboulhoda, S. J.; Reiners, I.; Wilken, J.; Henin, F.; Martens, J.; Muzart, J. Tetrahedron: Asymmetry 1998, 9, 1847; (g) Matsumoto, K.; Tsutsumi, S.; Ihori, T.; Ohta, H. J. Am. Chem. Soc. 1990, 112, 9614; (h) Fujii, I.; Lerner, R. A.; Janda, K. D. J. Am. Chem. Soc. 1991, 113, 8528; (i) Potin, D.; Williams, K.; Rebek, J. Angew. Chem., Int. Ed. Engl. 1990, 29, 1420; (j) Roy, O.; Riahi, A.; Hénin, F.; Muzart, J. Eur. J. Org. Chem. 2002, 3986; (k) Landais, Y.; Zekri, E. Eur. J. Org. Chem. 2002, 4037.
30. Harrison I.T., Lewis B., Nelson P., Rooks W., Roszkowoski A., Tomolonis A., Fried J.H. J. Med. Chem. 13:1970;203.
31. Riegl J., Maddox M.L., Harrison I.T. J. Med. Chem. 17:1974;377.
32. Giordano C., Castaldi G., Uggeri F. Angew. Chem., Int. Ed. Engl. 23:1984;413.
33. Gu Q.-M., Chen C.-S. Tetrahedron Lett. 27:1986;1763.
34. Giordano C., Castaldi G., Cavicchioli S., Villa M. Tetrahedron. 45:1989;4243.
35. Sonawane H.R., Bellur N.S., Ahuja J.R., Kulkarni D.G. Tetrahedron: Asymmetry. 3:1992;163.
36. Manimaran T., Stahly P. Tetrahedron: Asymmetry. 4:1993;1949.
37. Huang W.-C., Tsai S.-W., Chang C.-S. J. Chin. Inst. Chem. Engrs. 29:1998;153.
38. Cf. March J. Advanced Organic Chemistry. 3rd ed. 1985;348 Wiley, New York.
39. 3): δ 18.6, 28.2, 46.3, 55.3, 68.1, 80.6, 105.6, 118.9, 125.7, 126.3, 127.1, 129.1, 129.4, 132.5, 136.4, 157.6, 174.1.
40. 3), 92% ee.
41. For a review on the use of α-phenylethylamine as resolving agent, see: Juaristi E., Escalante J., León-Romo J.L., Reyes A. Tetrahedron: Asymmetry. 9:1998;715.
42. See also: Reyes A., Juaristi E. Synth. Commun. 25:1995;1053.
43. For a review on the use of α-phenylethylamine as chiral auxiliary, see: Juaristi E., León-Romo J.L., Reyes A., Escalante J. Tetrahedron: Asymmetry. 10:1999;2441.
44. 3): δ 21.9, 22.1, 40.6, 40.8, 49.9, 50.2, 117.6, 120.4, 121.9, 127.5, 129.1, 129.2, 130.4, 142.6, 155.9, 179.8.
45. 2-symmetric, chiral ligands in asymmetric synthesis, see: Whitesell J.K. Chem. Rev. 89:1989;1581.
46. 4 the Z configured enolates 2-4-Li are formed upon treatment of 2-4 with LDA.
47. 16 stereoinduction in the proton transfer from (S)-10 and (S,S)-11 to prochiral enolates 2-4-Li.
48. For a definition of the like/unlike stereochemical descriptors, see: Seebach D., Prelog V. Angew. Chem., Int. Ed. Engl. 21:1982;654.