Stereocontrolled Reactions Mediated by a Remote Sulfoxide Group: Synthesis of Optically Pure anti-β-Amino Alcohols

Organic Letters

Volumn 5, Issue 23, 2003, Pages 4513-4516

  García Ruano, José L ^a   Alemán, José ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AMINOALCOHOL; SULFOXIDE;

ARTICLE; CHEMICAL REACTION; CHIRALITY; ENANTIOMER; OXYGENATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0344496706     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0358410     Document Type: Article

References (54)

1. Relevant bioactive naturally occurring amino alcohols: (a) Nikolau, K. C.; Mitchel, H. J.; van Delft, F. L.; Rubsam, F.; Rodriguez, R. M. Angew. Chem., Int. Ed. 1998, 37, 1871. (b) Heightman, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. 1998, 38, 750. (c) Kolter, T.; Sandhoff, K. Angew. Chem., Int. Ed. 1998, 38, 1532. (d) Bergmeier, S. C. Tetrahedron 2000, 56, 2561.
2. Relevant bioactive naturally occurring amino alcohols: (a) Nikolau, K. C.; Mitchel, H. J.; van Delft, F. L.; Rubsam, F.; Rodriguez, R. M. Angew. Chem., Int. Ed. 1998, 37, 1871. (b) Heightman, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. 1998, 38, 750. (c) Kolter, T.; Sandhoff, K. Angew. Chem., Int. Ed. 1998, 38, 1532. (d) Bergmeier, S. C. Tetrahedron 2000, 56, 2561.
3. Relevant bioactive naturally occurring amino alcohols: (a) Nikolau, K. C.; Mitchel, H. J.; van Delft, F. L.; Rubsam, F.; Rodriguez, R. M. Angew. Chem., Int. Ed. 1998, 37, 1871. (b) Heightman, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. 1998, 38, 750. (c) Kolter, T.; Sandhoff, K. Angew. Chem., Int. Ed. 1998, 38, 1532. (d) Bergmeier, S. C. Tetrahedron 2000, 56, 2561.
4. Relevant bioactive naturally occurring amino alcohols: (a) Nikolau, K. C.; Mitchel, H. J.; van Delft, F. L.; Rubsam, F.; Rodriguez, R. M. Angew. Chem., Int. Ed. 1998, 37, 1871. (b) Heightman, T. D.; Vasella, A. T. Angew. Chem., Int. Ed. 1998, 38, 750. (c) Kolter, T.; Sandhoff, K. Angew. Chem., Int. Ed. 1998, 38, 1532. (d) Bergmeier, S. C. Tetrahedron 2000, 56, 2561.
5. Yuki, Y.; Saigo, K.; Tachibana, K.; Hasegava, M. Chem. Lett. 1986, 1347.
6. Recent reviews: (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. (b) Bloch, R. Chem. Rev. 1998, 98, 1407. (c) Reetz, M. T. Chem. Rev. 1999, 99, 1121. (d) Comprehensive Asymmetric Catalyst; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999. (e) Ojima, I. Catalytic Asymmetric Synthesis, 2nd ed.; VCH: New York, 2000. (f) Bergmeier, S. C. Tetrahedron 2000, 56, 2561. (g) Bonini, C.; Righi, G. Tetrahedron 2002, 58, 4981. (h) Tang, Z.; Jiang, F.; Yu, L.-T.; Xin, C.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262.
7. Recent reviews: (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. (b) Bloch, R. Chem. Rev. 1998, 98, 1407. (c) Reetz, M. T. Chem. Rev. 1999, 99, 1121. (d) Comprehensive Asymmetric Catalyst; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999. (e) Ojima, I. Catalytic Asymmetric Synthesis, 2nd ed.; VCH: New York, 2000. (f) Bergmeier, S. C. Tetrahedron 2000, 56, 2561. (g) Bonini, C.; Righi, G. Tetrahedron 2002, 58, 4981. (h) Tang, Z.; Jiang, F.; Yu, L.-T.; Xin, C.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262.
8. Recent reviews: (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. (b) Bloch, R. Chem. Rev. 1998, 98, 1407. (c) Reetz, M. T. Chem. Rev. 1999, 99, 1121. (d) Comprehensive Asymmetric Catalyst; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999. (e) Ojima, I. Catalytic Asymmetric Synthesis, 2nd ed.; VCH: New York, 2000. (f) Bergmeier, S. C. Tetrahedron 2000, 56, 2561. (g) Bonini, C.; Righi, G. Tetrahedron 2002, 58, 4981. (h) Tang, Z.; Jiang, F.; Yu, L.-T.; Xin, C.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262.
9. Recent reviews: (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. (b) Bloch, R. Chem. Rev. 1998, 98, 1407. (c) Reetz, M. T. Chem. Rev. 1999, 99, 1121. (d) Comprehensive Asymmetric Catalyst; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999. (e) Ojima, I. Catalytic Asymmetric Synthesis, 2nd ed.; VCH: New York, 2000. (f) Bergmeier, S. C. Tetrahedron 2000, 56, 2561. (g) Bonini, C.; Righi, G. Tetrahedron 2002, 58, 4981. (h) Tang, Z.; Jiang, F.; Yu, L.-T.; Xin, C.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262.
10. Recent reviews: (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. (b) Bloch, R. Chem. Rev. 1998, 98, 1407. (c) Reetz, M. T. Chem. Rev. 1999, 99, 1121. (d) Comprehensive Asymmetric Catalyst; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999. (e) Ojima, I. Catalytic Asymmetric Synthesis, 2nd ed.; VCH: New York, 2000. (f) Bergmeier, S. C. Tetrahedron 2000, 56, 2561. (g) Bonini, C.; Righi, G. Tetrahedron 2002, 58, 4981. (h) Tang, Z.; Jiang, F.; Yu, L.-T.; Xin, C.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262.
11. Recent reviews: (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. (b) Bloch, R. Chem. Rev. 1998, 98, 1407. (c) Reetz, M. T. Chem. Rev. 1999, 99, 1121. (d) Comprehensive Asymmetric Catalyst; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999. (e) Ojima, I. Catalytic Asymmetric Synthesis, 2nd ed.; VCH: New York, 2000. (f) Bergmeier, S. C. Tetrahedron 2000, 56, 2561. (g) Bonini, C.; Righi, G. Tetrahedron 2002, 58, 4981. (h) Tang, Z.; Jiang, F.; Yu, L.-T.; Xin, C.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262.
12. Recent reviews: (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. (b) Bloch, R. Chem. Rev. 1998, 98, 1407. (c) Reetz, M. T. Chem. Rev. 1999, 99, 1121. (d) Comprehensive Asymmetric Catalyst; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999. (e) Ojima, I. Catalytic Asymmetric Synthesis, 2nd ed.; VCH: New York, 2000. (f) Bergmeier, S. C. Tetrahedron 2000, 56, 2561. (g) Bonini, C.; Righi, G. Tetrahedron 2002, 58, 4981. (h) Tang, Z.; Jiang, F.; Yu, L.-T.; Xin, C.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262.
13. Recent reviews: (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835. (b) Bloch, R. Chem. Rev. 1998, 98, 1407. (c) Reetz, M. T. Chem. Rev. 1999, 99, 1121. (d) Comprehensive Asymmetric Catalyst; Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds.; Springer-Verlag: Berlin, 1999. (e) Ojima, I. Catalytic Asymmetric Synthesis, 2nd ed.; VCH: New York, 2000. (f) Bergmeier, S. C. Tetrahedron 2000, 56, 2561. (g) Bonini, C.; Righi, G. Tetrahedron 2002, 58, 4981. (h) Tang, Z.; Jiang, F.; Yu, L.-T.; Xin, C.; Gong, L.-Z.; Mi, A.-Q.; Jiang, Y.-Z.; Wu, Y.-D. J. Am. Chem. Soc. 2003, 125, 5262.
14. Aoyagi, Y.; Agata, N.; Shibata, N.; Horiguchi, M.; Williams, R. M. Tetrahedron Lett. 2000, 41, 10159.
15. Shimizu, M.; Tsukamoto, K.; Matsutani, T.; Fujisawa, T. Tetrahedron 1998, 54, 10265.
16. (a) Sharpless, K. B.; Gao, Y. J. Am. Chem. Soc. 1988, 110, 7538.
17. (b) Sharpless, K. B.; Chang, H. T. Tetrahedron Lett. 1996, 37, 3129.
18. (c) Nicolaou, K. C.; Huang, X.; Zinder, S. C.; Rao, B. P.; Bella, M. V.; Reddy, M. V. Angew. Chem., Int. Ed. 2002, 41, 834.
19. (a) Li, G.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 451-454.
20. (b) Andrsson, M. A.; Epple R.; Fokin, V. V.; Sharpless, K. B. Angew. Chem., Int. Ed. 2002, 41, 472.
21. (a) Jacobsen, E. N. Acc. Chem. Res. 2000, 33, 421.
22. (b) Lane, B. S.; Burgess, K. Chem. Rev. 2003, 103, 2457.
23. (a) Tanaka, Y.; Taniguchi, N.; Uemura, M. Org. Lett. 2002, 4, 835-838.
24. (b) Tanaka, Y.; Taniguchi, N.; Kimura, T.; Uemura, M. J. Org. Chem. 2002, 67, 9227.
25. (a) Trost, B. M.; Yeh, V. S. C.; Ito, H.; Bremeyer, N. Org. Lett. 2002, 4, 2621.
26. (b) Sasai, H.; Tokunaga, T.; Watanabe, S.; Suzuki, T.; Itoh, N.; Shibasaki, M. J. Org. Chem. 1995, 60, 7388.
27. (c) Horikawa, M.; Buch-Petersen, J.; Corey, E. J. Tetrahedron Lett. 1999, 40, 3843.
28. (a) Arrasate, S.; Lete, E.; Sotomayor, N. Tetrahedron: Asymmetry 2002, 13, 311.
29. (b) Kobayashi, S.; Ishitani, H.; Ueno, M. J. Am. Chem. Soc. 1998, 120, 431.
30. These compounds have shown their efficiency in controlling the stereoselectivity of nucleophilic additions. The most significant contributions are those from Davis's group and Ellman's group: (a) Davis, F. A.; Zhou, P.; Chen, B. C. Chem. Soc. Rev. 1998, 27, 13. (b) Davis, F. A.; Wu, Y.; Yan, H.; McCoull, W.; Prasad, K. R. J. Org. Chem. 2003, 68, 2410. (c) Davis, F. A.; Prasad, K. R.; Nolt, M. B.; Wu, Y. Org. Lett. 2003, 5, 925. (d) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984. (e) Ellman, J. A. Pure Appl. Chem. 2003, 75, 39. (f) Weix, D. J.; Ellman, J. A. Org. Lett. 2003, 5, 1317. (e) Schenkel, L. B.; Ellman, J. A. Org. Lett. 2003, 5, 545.
31. These compounds have shown their efficiency in controlling the stereoselectivity of nucleophilic additions. The most significant contributions are those from Davis's group and Ellman's group: (a) Davis, F. A.; Zhou, P.; Chen, B. C. Chem. Soc. Rev. 1998, 27, 13. (b) Davis, F. A.; Wu, Y.; Yan, H.; McCoull, W.; Prasad, K. R. J. Org. Chem. 2003, 68, 2410. (c) Davis, F. A.; Prasad, K. R.; Nolt, M. B.; Wu, Y. Org. Lett. 2003, 5, 925. (d) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984. (e) Ellman, J. A. Pure Appl. Chem. 2003, 75, 39. (f) Weix, D. J.; Ellman, J. A. Org. Lett. 2003, 5, 1317. (e) Schenkel, L. B.; Ellman, J. A. Org. Lett. 2003, 5, 545.
32. These compounds have shown their efficiency in controlling the stereoselectivity of nucleophilic additions. The most significant contributions are those from Davis's group and Ellman's group: (a) Davis, F. A.; Zhou, P.; Chen, B. C. Chem. Soc. Rev. 1998, 27, 13. (b) Davis, F. A.; Wu, Y.; Yan, H.; McCoull, W.; Prasad, K. R. J. Org. Chem. 2003, 68, 2410. (c) Davis, F. A.; Prasad, K. R.; Nolt, M. B.; Wu, Y. Org. Lett. 2003, 5, 925. (d) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984. (e) Ellman, J. A. Pure Appl. Chem. 2003, 75, 39. (f) Weix, D. J.; Ellman, J. A. Org. Lett. 2003, 5, 1317. (e) Schenkel, L. B.; Ellman, J. A. Org. Lett. 2003, 5, 545.
33. These compounds have shown their efficiency in controlling the stereoselectivity of nucleophilic additions. The most significant contributions are those from Davis's group and Ellman's group: (a) Davis, F. A.; Zhou, P.; Chen, B. C. Chem. Soc. Rev. 1998, 27, 13. (b) Davis, F. A.; Wu, Y.; Yan, H.; McCoull, W.; Prasad, K. R. J. Org. Chem. 2003, 68, 2410. (c) Davis, F. A.; Prasad, K. R.; Nolt, M. B.; Wu, Y. Org. Lett. 2003, 5, 925. (d) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984. (e) Ellman, J. A. Pure Appl. Chem. 2003, 75, 39. (f) Weix, D. J.; Ellman, J. A. Org. Lett. 2003, 5, 1317. (e) Schenkel, L. B.; Ellman, J. A. Org. Lett. 2003, 5, 545.
34. These compounds have shown their efficiency in controlling the stereoselectivity of nucleophilic additions. The most significant contributions are those from Davis's group and Ellman's group: (a) Davis, F. A.; Zhou, P.; Chen, B. C. Chem. Soc. Rev. 1998, 27, 13. (b) Davis, F. A.; Wu, Y.; Yan, H.; McCoull, W.; Prasad, K. R. J. Org. Chem. 2003, 68, 2410. (c) Davis, F. A.; Prasad, K. R.; Nolt, M. B.; Wu, Y. Org. Lett. 2003, 5, 925. (d) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984. (e) Ellman, J. A. Pure Appl. Chem. 2003, 75, 39. (f) Weix, D. J.; Ellman, J. A. Org. Lett. 2003, 5, 1317. (e) Schenkel, L. B.; Ellman, J. A. Org. Lett. 2003, 5, 545.
35. These compounds have shown their efficiency in controlling the stereoselectivity of nucleophilic additions. The most significant contributions are those from Davis's group and Ellman's group: (a) Davis, F. A.; Zhou, P.; Chen, B. C. Chem. Soc. Rev. 1998, 27, 13. (b) Davis, F. A.; Wu, Y.; Yan, H.; McCoull, W.; Prasad, K. R. J. Org. Chem. 2003, 68, 2410. (c) Davis, F. A.; Prasad, K. R.; Nolt, M. B.; Wu, Y. Org. Lett. 2003, 5, 925. (d) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984. (e) Ellman, J. A. Pure Appl. Chem. 2003, 75, 39. (f) Weix, D. J.; Ellman, J. A. Org. Lett. 2003, 5, 1317. (e) Schenkel, L. B.; Ellman, J. A. Org. Lett. 2003, 5, 545.
36. These compounds have shown their efficiency in controlling the stereoselectivity of nucleophilic additions. The most significant contributions are those from Davis's group and Ellman's group: (a) Davis, F. A.; Zhou, P.; Chen, B. C. Chem. Soc. Rev. 1998, 27, 13. (b) Davis, F. A.; Wu, Y.; Yan, H.; McCoull, W.; Prasad, K. R. J. Org. Chem. 2003, 68, 2410. (c) Davis, F. A.; Prasad, K. R.; Nolt, M. B.; Wu, Y. Org. Lett. 2003, 5, 925. (d) Ellman, J. A.; Owens, T. D.; Tang, T. P. Acc. Chem. Res. 2002, 35, 984. (e) Ellman, J. A. Pure Appl. Chem. 2003, 75, 39. (f) Weix, D. J.; Ellman, J. A. Org. Lett. 2003, 5, 1317. (e) Schenkel, L. B.; Ellman, J. A. Org. Lett. 2003, 5, 545.
37. García Ruano, J. L.; Aranda, M.; Carreno, M. C.; Toledo, M. A. Angew. Chem., Int. Ed. 2000, 39, 2736.
38. García Ruano, J. L.; Alemán, J.; Soriano J. F. Org. Lett. 2003, 5, 677.
39. The higher de observed from α-sylilated carbanions with respect to their corresponding alkyl derivatives (see ref 13) could be explained with this model by assuming the OTIPS group is larger than the Me one. However, the competence between transition states such as TS-A with others involving eight-membered rings cannot be disregarded and it is currently under study with other electrophiles.
40. R less stable (see Figure 1).
41. NMR spectra of the reaction crude are very clean and revealed the almost quantitative conversion in all the cases, even starting from 1j. Indeed, compound 3j was completely destroyed during chromatographic purification
42. The authors have deposited atomic coordinates for 3i with the Cambridge Crystallographic Data Centre (deposition number CCDC 208928). The coordinates can be obtained, on request, from the Director, Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge Cb2 1EZ, UK.
43. Kanematsu, K.; Sasaki, T. J. Med. Chem. 1966, 847.
44. Fernandez, I.; Khiar, N. Chem. Rev. 2003, 103, 3651.
45. Recent references about the use of sulfoxides as chiral ligands: (a) Lai, C-Y.; Mak, W.-L.; Chan, E. Y. Y.; Sau, Y.-K.; Zhang, Q.-F.; Lo, S. M. F.; Williams, I. D.; Leung, W.-H. Inorg. Chem. 2003, 42, 5863. (b) Ekegren, J. K.; Roth, P.; Kallstrom, K.; Tarnai, T.; Andersson, P. G. Org. Biomol. Chem. 2003, 1, 358. (c) Rowlands, G. J. Synlett 2003, 236. (d) Watanabe, K.; Hirasawa, T.; Hiroi, K. Chem. Pharm. Bull. 2002, 50, 372. (e) Priego, J.; Mancheno, O.; Cabrera, S.; Carretero, J. C. J. Org. Chem. 2002, 67, 1346. Recent references about the use of thioethers as chiral ligands: (f) Masdeu-Bulto, A. M.; Dieguez, M.; Martin, E.; Gomez, M. Coord. Chem. Rev. 2003, 242, 159. (g) Verdaguer, X.; Pericas, M. A.; Riera, A.; Maestro, M. A.; Mahia, J. Organometallics 2003, 22, 1868. (h) Dervisi, A.; Jenkins, R. L.; Malik, K. M. A.; Hursthouse, M. B.; Coles, S. Dalton Trans. 2003, 1133.
46. Recent references about the use of sulfoxides as chiral ligands: (a) Lai, C-Y.; Mak, W.-L.; Chan, E. Y. Y.; Sau, Y.-K.; Zhang, Q.-F.; Lo, S. M. F.; Williams, I. D.; Leung, W.-H. Inorg. Chem. 2003, 42, 5863. (b) Ekegren, J. K.; Roth, P.; Kallstrom, K.; Tarnai, T.; Andersson, P. G. Org. Biomol. Chem. 2003, 1, 358. (c) Rowlands, G. J. Synlett 2003, 236. (d) Watanabe, K.; Hirasawa, T.; Hiroi, K. Chem. Pharm. Bull. 2002, 50, 372. (e) Priego, J.; Mancheno, O.; Cabrera, S.; Carretero, J. C. J. Org. Chem. 2002, 67, 1346. Recent references about the use of thioethers as chiral ligands: (f) Masdeu-Bulto, A. M.; Dieguez, M.; Martin, E.; Gomez, M. Coord. Chem. Rev. 2003, 242, 159. (g) Verdaguer, X.; Pericas, M. A.; Riera, A.; Maestro, M. A.; Mahia, J. Organometallics 2003, 22, 1868. (h) Dervisi, A.; Jenkins, R. L.; Malik, K. M. A.; Hursthouse, M. B.; Coles, S. Dalton Trans. 2003, 1133.
47. Recent references about the use of sulfoxides as chiral ligands: (a) Lai, C-Y.; Mak, W.-L.; Chan, E. Y. Y.; Sau, Y.-K.; Zhang, Q.-F.; Lo, S. M. F.; Williams, I. D.; Leung, W.-H. Inorg. Chem. 2003, 42, 5863. (b) Ekegren, J. K.; Roth, P.; Kallstrom, K.; Tarnai, T.; Andersson, P. G. Org. Biomol. Chem. 2003, 1, 358. (c) Rowlands, G. J. Synlett 2003, 236. (d) Watanabe, K.; Hirasawa, T.; Hiroi, K. Chem. Pharm. Bull. 2002, 50, 372. (e) Priego, J.; Mancheno, O.; Cabrera, S.; Carretero, J. C. J. Org. Chem. 2002, 67, 1346. Recent references about the use of thioethers as chiral ligands: (f) Masdeu-Bulto, A. M.; Dieguez, M.; Martin, E.; Gomez, M. Coord. Chem. Rev. 2003, 242, 159. (g) Verdaguer, X.; Pericas, M. A.; Riera, A.; Maestro, M. A.; Mahia, J. Organometallics 2003, 22, 1868. (h) Dervisi, A.; Jenkins, R. L.; Malik, K. M. A.; Hursthouse, M. B.; Coles, S. Dalton Trans. 2003, 1133.
48. Recent references about the use of sulfoxides as chiral ligands: (a) Lai, C-Y.; Mak, W.-L.; Chan, E. Y. Y.; Sau, Y.-K.; Zhang, Q.-F.; Lo, S. M. F.; Williams, I. D.; Leung, W.-H. Inorg. Chem. 2003, 42, 5863. (b) Ekegren, J. K.; Roth, P.; Kallstrom, K.; Tarnai, T.; Andersson, P. G. Org. Biomol. Chem. 2003, 1, 358. (c) Rowlands, G. J. Synlett 2003, 236. (d) Watanabe, K.; Hirasawa, T.; Hiroi, K. Chem. Pharm. Bull. 2002, 50, 372. (e) Priego, J.; Mancheno, O.; Cabrera, S.; Carretero, J. C. J. Org. Chem. 2002, 67, 1346. Recent references about the use of thioethers as chiral ligands: (f) Masdeu-Bulto, A. M.; Dieguez, M.; Martin, E.; Gomez, M. Coord. Chem. Rev. 2003, 242, 159. (g) Verdaguer, X.; Pericas, M. A.; Riera, A.; Maestro, M. A.; Mahia, J. Organometallics 2003, 22, 1868. (h) Dervisi, A.; Jenkins, R. L.; Malik, K. M. A.; Hursthouse, M. B.; Coles, S. Dalton Trans. 2003, 1133.
49. Recent references about the use of sulfoxides as chiral ligands: (a) Lai, C-Y.; Mak, W.-L.; Chan, E. Y. Y.; Sau, Y.-K.; Zhang, Q.-F.; Lo, S. M. F.; Williams, I. D.; Leung, W.-H. Inorg. Chem. 2003, 42, 5863. (b) Ekegren, J. K.; Roth, P.; Kallstrom, K.; Tarnai, T.; Andersson, P. G. Org. Biomol. Chem. 2003, 1, 358. (c) Rowlands, G. J. Synlett 2003, 236. (d) Watanabe, K.; Hirasawa, T.; Hiroi, K. Chem. Pharm. Bull. 2002, 50, 372. (e) Priego, J.; Mancheno, O.; Cabrera, S.; Carretero, J. C. J. Org. Chem. 2002, 67, 1346. Recent references about the use of thioethers as chiral ligands: (f) Masdeu-Bulto, A. M.; Dieguez, M.; Martin, E.; Gomez, M. Coord. Chem. Rev. 2003, 242, 159. (g) Verdaguer, X.; Pericas, M. A.; Riera, A.; Maestro, M. A.; Mahia, J. Organometallics 2003, 22, 1868. (h) Dervisi, A.; Jenkins, R. L.; Malik, K. M. A.; Hursthouse, M. B.; Coles, S. Dalton Trans. 2003, 1133.
50. Recent references about the use of sulfoxides as chiral ligands: (a) Lai, C-Y.; Mak, W.-L.; Chan, E. Y. Y.; Sau, Y.-K.; Zhang, Q.-F.; Lo, S. M. F.; Williams, I. D.; Leung, W.-H. Inorg. Chem. 2003, 42, 5863. (b) Ekegren, J. K.; Roth, P.; Kallstrom, K.; Tarnai, T.; Andersson, P. G. Org. Biomol. Chem. 2003, 1, 358. (c) Rowlands, G. J. Synlett 2003, 236. (d) Watanabe, K.; Hirasawa, T.; Hiroi, K. Chem. Pharm. Bull. 2002, 50, 372. (e) Priego, J.; Mancheno, O.; Cabrera, S.; Carretero, J. C. J. Org. Chem. 2002, 67, 1346. Recent references about the use of thioethers as chiral ligands: (f) Masdeu-Bulto, A. M.; Dieguez, M.; Martin, E.; Gomez, M. Coord. Chem. Rev. 2003, 242, 159. (g) Verdaguer, X.; Pericas, M. A.; Riera, A.; Maestro, M. A.; Mahia, J. Organometallics 2003, 22, 1868. (h) Dervisi, A.; Jenkins, R. L.; Malik, K. M. A.; Hursthouse, M. B.; Coles, S. Dalton Trans. 2003, 1133.
51. Recent references about the use of sulfoxides as chiral ligands: (a) Lai, C-Y.; Mak, W.-L.; Chan, E. Y. Y.; Sau, Y.-K.; Zhang, Q.-F.; Lo, S. M. F.; Williams, I. D.; Leung, W.-H. Inorg. Chem. 2003, 42, 5863. (b) Ekegren, J. K.; Roth, P.; Kallstrom, K.; Tarnai, T.; Andersson, P. G. Org. Biomol. Chem. 2003, 1, 358. (c) Rowlands, G. J. Synlett 2003, 236. (d) Watanabe, K.; Hirasawa, T.; Hiroi, K. Chem. Pharm. Bull. 2002, 50, 372. (e) Priego, J.; Mancheno, O.; Cabrera, S.; Carretero, J. C. J. Org. Chem. 2002, 67, 1346. Recent references about the use of thioethers as chiral ligands: (f) Masdeu-Bulto, A. M.; Dieguez, M.; Martin, E.; Gomez, M. Coord. Chem. Rev. 2003, 242, 159. (g) Verdaguer, X.; Pericas, M. A.; Riera, A.; Maestro, M. A.; Mahia, J. Organometallics 2003, 22, 1868. (h) Dervisi, A.; Jenkins, R. L.; Malik, K. M. A.; Hursthouse, M. B.; Coles, S. Dalton Trans. 2003, 1133.
52. Recent references about the use of sulfoxides as chiral ligands: (a) Lai, C-Y.; Mak, W.-L.; Chan, E. Y. Y.; Sau, Y.-K.; Zhang, Q.-F.; Lo, S. M. F.; Williams, I. D.; Leung, W.-H. Inorg. Chem. 2003, 42, 5863. (b) Ekegren, J. K.; Roth, P.; Kallstrom, K.; Tarnai, T.; Andersson, P. G. Org. Biomol. Chem. 2003, 1, 358. (c) Rowlands, G. J. Synlett 2003, 236. (d) Watanabe, K.; Hirasawa, T.; Hiroi, K. Chem. Pharm. Bull. 2002, 50, 372. (e) Priego, J.; Mancheno, O.; Cabrera, S.; Carretero, J. C. J. Org. Chem. 2002, 67, 1346. Recent references about the use of thioethers as chiral ligands: (f) Masdeu-Bulto, A. M.; Dieguez, M.; Martin, E.; Gomez, M. Coord. Chem. Rev. 2003, 242, 159. (g) Verdaguer, X.; Pericas, M. A.; Riera, A.; Maestro, M. A.; Mahia, J. Organometallics 2003, 22, 1868. (h) Dervisi, A.; Jenkins, R. L.; Malik, K. M. A.; Hursthouse, M. B.; Coles, S. Dalton Trans. 2003, 1133.
53. Partial epimerization was not observed in the reactions from 6 and 9 indicated in Scheme 3.
54. García Ruano, J. L.; Paredes, C. G.; Hamdouchi, C. Tetrahedron: Asymmetry 1999, 10, 2935 and references therein.