Synthesis, structure, and reactivity of the first enantiomerically pure ortho-metalated Rhodium(II) dimer [3]

Journal of the American Chemical Society

Volumn 121, Issue 4, 1999, Pages 860-861

  Taber, Douglass F ^a   Malcolm, Scott C ^a   Bieger, Klaus ^b   Lahuerta, Pascual ^b   Sanaú, Mercedes ^b   Stiriba, Salah Eddine ^b   Pérez Prieto, Julia ^b   Monge, M Angeles ^c  

^a UNIVERSITY OF DELAWARE   (United States)

^b UNIVERSITY OF VALENCIA   (Spain)

^c INSTITUTO DE CIENCIA DE MATERIALES DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

DIMER; RHODIUM; RHODIUM COMPLEX;

CATALYST; CHEMICAL REACTION; CHIRALITY; CYCLIZATION; ENANTIOMER; LETTER; SYNTHESIS;

EID: 0033518590     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9819559     Document Type: Letter

References (35)

1. For recent and highly readable reviews on this topic, see: (a) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091. (b) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385. (c) Padwa, A.; Austin D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (d) McKervey, M. A.; Doyle M. P. J. Chem. Soc., Chem. Commun. 1997, 983. (e) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon Press: New York, 1995; Vol. 12, Chapter 5.2, p 421. (f) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388. (g) Doyle, M. P. Chem. Rev. 1986, 86, 919. (h) Doyle, M. P. Chem. Res. 1986, 19, 348.
2. For recent and highly readable reviews on this topic, see: (a) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091. (b) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385. (c) Padwa, A.; Austin D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (d) McKervey, M. A.; Doyle M. P. J. Chem. Soc., Chem. Commun. 1997, 983. (e) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon Press: New York, 1995; Vol. 12, Chapter 5.2, p 421. (f) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388. (g) Doyle, M. P. Chem. Rev. 1986, 86, 919. (h) Doyle, M. P. Chem. Res. 1986, 19, 348.
3. For recent and highly readable reviews on this topic, see: (a) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091. (b) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385. (c) Padwa, A.; Austin D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (d) McKervey, M. A.; Doyle M. P. J. Chem. Soc., Chem. Commun. 1997, 983. (e) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon Press: New York, 1995; Vol. 12, Chapter 5.2, p 421. (f) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388. (g) Doyle, M. P. Chem. Rev. 1986, 86, 919. (h) Doyle, M. P. Chem. Res. 1986, 19, 348.
4. For recent and highly readable reviews on this topic, see: (a) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091. (b) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385. (c) Padwa, A.; Austin D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (d) McKervey, M. A.; Doyle M. P. J. Chem. Soc., Chem. Commun. 1997, 983. (e) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon Press: New York, 1995; Vol. 12, Chapter 5.2, p 421. (f) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388. (g) Doyle, M. P. Chem. Rev. 1986, 86, 919. (h) Doyle, M. P. Chem. Res. 1986, 19, 348.
5. For recent and highly readable reviews on this topic, see: (a) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091. (b) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385. (c) Padwa, A.; Austin D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (d) McKervey, M. A.; Doyle M. P. J. Chem. Soc., Chem. Commun. 1997, 983. (e) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon Press: New York, 1995; Vol. 12, Chapter 5.2, p 421. (f) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388. (g) Doyle, M. P. Chem. Rev. 1986, 86, 919. (h) Doyle, M. P. Chem. Res. 1986, 19, 348.
6. For recent and highly readable reviews on this topic, see: (a) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091. (b) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385. (c) Padwa, A.; Austin D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (d) McKervey, M. A.; Doyle M. P. J. Chem. Soc., Chem. Commun. 1997, 983. (e) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon Press: New York, 1995; Vol. 12, Chapter 5.2, p 421. (f) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388. (g) Doyle, M. P. Chem. Rev. 1986, 86, 919. (h) Doyle, M. P. Chem. Res. 1986, 19, 348.
7. For recent and highly readable reviews on this topic, see: (a) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091. (b) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385. (c) Padwa, A.; Austin D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (d) McKervey, M. A.; Doyle M. P. J. Chem. Soc., Chem. Commun. 1997, 983. (e) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon Press: New York, 1995; Vol. 12, Chapter 5.2, p 421. (f) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388. (g) Doyle, M. P. Chem. Rev. 1986, 86, 919. (h) Doyle, M. P. Chem. Res. 1986, 19, 348.
8. For recent and highly readable reviews on this topic, see: (a) Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091. (b) Padwa, A.; Krumpe, K. E. Tetrahedron 1992, 48, 5385. (c) Padwa, A.; Austin D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797. (d) McKervey, M. A.; Doyle M. P. J. Chem. Soc., Chem. Commun. 1997, 983. (e) Doyle, M. P. In Comprehensive Organometallic Chemistry II; Hegedus, L. S., Ed.; Pergamon Press: New York, 1995; Vol. 12, Chapter 5.2, p 421. (f) Corey, E. J.; Guzman-Perez, A. Angew. Chem., Int. Ed. 1998, 37, 388. (g) Doyle, M. P. Chem. Rev. 1986, 86, 919. (h) Doyle, M. P. Chem. Res. 1986, 19, 348.
9. For results with rhodium(II) compounds that possess chiral oxazolidone or pyrrolidone as bridging ligands, see: (a) Doyle, M. P., Winchester, W. R.; Hoorn, J. A. A.; Lynch, V.; Simonsen, S. H.; Ghosh, R. J. Am. Chem. Soc. 1993, 115, 9968. (b) Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, Q. L.; Zhou, S. F.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763. (c) Doyle, M. P. Aldrichim. Acta 1996, 29, 3 and references therein. (d) Doyle, M. P.; Dyatkin, A. B.; Protopopova, M. N.; Yang, C. I.; Miertschin, C. S.; Winchester, W. R.; Simonsen, S. H.; Lynch, V.; Ghosh, R. Rec. Trav. Chim. Pays-Bas 1995, 114, 163. (e) Doyle, M. P. Peterson, C. S.; Parker, D. L. Angew. Chem., Int. Ed. Engl. 1996, 35, 1334.
10. For results with rhodium(II) compounds that possess chiral oxazolidone or pyrrolidone as bridging ligands, see: (a) Doyle, M. P., Winchester, W. R.; Hoorn, J. A. A.; Lynch, V.; Simonsen, S. H.; Ghosh, R. J. Am. Chem. Soc. 1993, 115, 9968. (b) Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, Q. L.; Zhou, S. F.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763. (c) Doyle, M. P. Aldrichim. Acta 1996, 29, 3 and references therein. (d) Doyle, M. P.; Dyatkin, A. B.; Protopopova, M. N.; Yang, C. I.; Miertschin, C. S.; Winchester, W. R.; Simonsen, S. H.; Lynch, V.; Ghosh, R. Rec. Trav. Chim. Pays-Bas 1995, 114, 163. (e) Doyle, M. P. Peterson, C. S.; Parker, D. L. Angew. Chem., Int. Ed. Engl. 1996, 35, 1334.
11. For results with rhodium(II) compounds that possess chiral oxazolidone or pyrrolidone as bridging ligands, see: (a) Doyle, M. P., Winchester, W. R.; Hoorn, J. A. A.; Lynch, V.; Simonsen, S. H.; Ghosh, R. J. Am. Chem. Soc. 1993, 115, 9968. (b) Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, Q. L.; Zhou, S. F.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763. (c) Doyle, M. P. Aldrichim. Acta 1996, 29, 3 and references therein. (d) Doyle, M. P.; Dyatkin, A. B.; Protopopova, M. N.; Yang, C. I.; Miertschin, C. S.; Winchester, W. R.; Simonsen, S. H.; Lynch, V.; Ghosh, R. Rec. Trav. Chim. Pays-Bas 1995, 114, 163. (e) Doyle, M. P. Peterson, C. S.; Parker, D. L. Angew. Chem., Int. Ed. Engl. 1996, 35, 1334.
12. For results with rhodium(II) compounds that possess chiral oxazolidone or pyrrolidone as bridging ligands, see: (a) Doyle, M. P., Winchester, W. R.; Hoorn, J. A. A.; Lynch, V.; Simonsen, S. H.; Ghosh, R. J. Am. Chem. Soc. 1993, 115, 9968. (b) Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, Q. L.; Zhou, S. F.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763. (c) Doyle, M. P. Aldrichim. Acta 1996, 29, 3 and references therein. (d) Doyle, M. P.; Dyatkin, A. B.; Protopopova, M. N.; Yang, C. I.; Miertschin, C. S.; Winchester, W. R.; Simonsen, S. H.; Lynch, V.; Ghosh, R. Rec. Trav. Chim. Pays-Bas 1995, 114, 163. (e) Doyle, M. P. Peterson, C. S.; Parker, D. L. Angew. Chem., Int. Ed. Engl. 1996, 35, 1334.
13. For results with rhodium(II) compounds that possess chiral oxazolidone or pyrrolidone as bridging ligands, see: (a) Doyle, M. P., Winchester, W. R.; Hoorn, J. A. A.; Lynch, V.; Simonsen, S. H.; Ghosh, R. J. Am. Chem. Soc. 1993, 115, 9968. (b) Doyle, M. P.; Austin, R. E.; Bailey, A. S.; Dwyer, M. P.; Dyatkin, A. B.; Kalinin, A. V.; Kwan, M. M.; Liras, S.; Oalmann, C. J.; Pieters, R. J.; Protopopova, M. N.; Raab, C. E.; Roos, Q. L.; Zhou, S. F.; Martin, S. F. J. Am. Chem. Soc. 1995, 117, 5763. (c) Doyle, M. P. Aldrichim. Acta 1996, 29, 3 and references therein. (d) Doyle, M. P.; Dyatkin, A. B.; Protopopova, M. N.; Yang, C. I.; Miertschin, C. S.; Winchester, W. R.; Simonsen, S. H.; Lynch, V.; Ghosh, R. Rec. Trav. Chim. Pays-Bas 1995, 114, 163. (e) Doyle, M. P. Peterson, C. S.; Parker, D. L. Angew. Chem., Int. Ed. Engl. 1996, 35, 1334.
14. Rhodium(II) catalysts with binaphtholphosphate ligands have been reported: (a) Pirrung, M. C.; Zhang, J. Tetrahedron Lett. 1992, 33, 5987. (b) McCarthy, N.; McKervey, M. A.; Ye, T.; McCann, M.; Murphy, E.; Doyle, M. P. Tetrahedron Lett. 1992, 33, 5983.
15. Rhodium(II) catalysts with binaphtholphosphate ligands have been reported: (a) Pirrung, M. C.; Zhang, J. Tetrahedron Lett. 1992, 33, 5987. (b) McCarthy, N.; McKervey, M. A.; Ye, T.; McCann, M.; Murphy, E.; Doyle, M. P. Tetrahedron Lett. 1992, 33, 5983.
16. For reports on enantioselective catalysis by dirhodium complexes prepared from chiral carboxylic acids, see: (a) Kennedy, M.; McKervey, M. A.; Maguire, A. R.; Roos, G. H. P. J. Chem. Soc., Chem. Comm. 1990, 361. (b) Fernandez Garcia, C.; McKervey, M. A.; Ye, T. J. Chem. Soc. Chem. Commun. 1996, 1465. (c) Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.; Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6897. (d) Davies, H. M. L.; Matasi, J. J.; Hodges, L. M.; Huby, N. J. S.; Thornley, C.; Kong, N.; Houser, J. H. J. Org. Chem. 1997, 62, 1095. (e) Watanabe, N.; Ogawa, T.; Ohtake, Y.; Ikegami, S.; Hashimoto, S. Synlett 1996, 85. (f) Watanabe, N.; Ohtake, Y.; Hashimoto, S.; Shiro, M.; Ikegami, S. Tetrahedron Lett. 1995, 36, 1491.
17. For reports on enantioselective catalysis by dirhodium complexes prepared from chiral carboxylic acids, see: (a) Kennedy, M.; McKervey, M. A.; Maguire, A. R.; Roos, G. H. P. J. Chem. Soc., Chem. Comm. 1990, 361. (b) Fernandez Garcia, C.; McKervey, M. A.; Ye, T. J. Chem. Soc. Chem. Commun. 1996, 1465. (c) Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.; Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6897. (d) Davies, H. M. L.; Matasi, J. J.; Hodges, L. M.; Huby, N. J. S.; Thornley, C.; Kong, N.; Houser, J. H. J. Org. Chem. 1997, 62, 1095. (e) Watanabe, N.; Ogawa, T.; Ohtake, Y.; Ikegami, S.; Hashimoto, S. Synlett 1996, 85. (f) Watanabe, N.; Ohtake, Y.; Hashimoto, S.; Shiro, M.; Ikegami, S. Tetrahedron Lett. 1995, 36, 1491.
18. For reports on enantioselective catalysis by dirhodium complexes prepared from chiral carboxylic acids, see: (a) Kennedy, M.; McKervey, M. A.; Maguire, A. R.; Roos, G. H. P. J. Chem. Soc., Chem. Comm. 1990, 361. (b) Fernandez Garcia, C.; McKervey, M. A.; Ye, T. J. Chem. Soc. Chem. Commun. 1996, 1465. (c) Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.; Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6897. (d) Davies, H. M. L.; Matasi, J. J.; Hodges, L. M.; Huby, N. J. S.; Thornley, C.; Kong, N.; Houser, J. H. J. Org. Chem. 1997, 62, 1095. (e) Watanabe, N.; Ogawa, T.; Ohtake, Y.; Ikegami, S.; Hashimoto, S. Synlett 1996, 85. (f) Watanabe, N.; Ohtake, Y.; Hashimoto, S.; Shiro, M.; Ikegami, S. Tetrahedron Lett. 1995, 36, 1491.
19. For reports on enantioselective catalysis by dirhodium complexes prepared from chiral carboxylic acids, see: (a) Kennedy, M.; McKervey, M. A.; Maguire, A. R.; Roos, G. H. P. J. Chem. Soc., Chem. Comm. 1990, 361. (b) Fernandez Garcia, C.; McKervey, M. A.; Ye, T. J. Chem. Soc. Chem. Commun. 1996, 1465. (c) Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.; Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6897. (d) Davies, H. M. L.; Matasi, J. J.; Hodges, L. M.; Huby, N. J. S.; Thornley, C.; Kong, N.; Houser, J. H. J. Org. Chem. 1997, 62, 1095. (e) Watanabe, N.; Ogawa, T.; Ohtake, Y.; Ikegami, S.; Hashimoto, S. Synlett 1996, 85. (f) Watanabe, N.; Ohtake, Y.; Hashimoto, S.; Shiro, M.; Ikegami, S. Tetrahedron Lett. 1995, 36, 1491.
20. For reports on enantioselective catalysis by dirhodium complexes prepared from chiral carboxylic acids, see: (a) Kennedy, M.; McKervey, M. A.; Maguire, A. R.; Roos, G. H. P. J. Chem. Soc., Chem. Comm. 1990, 361. (b) Fernandez Garcia, C.; McKervey, M. A.; Ye, T. J. Chem. Soc. Chem. Commun. 1996, 1465. (c) Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.; Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6897. (d) Davies, H. M. L.; Matasi, J. J.; Hodges, L. M.; Huby, N. J. S.; Thornley, C.; Kong, N.; Houser, J. H. J. Org. Chem. 1997, 62, 1095. (e) Watanabe, N.; Ogawa, T.; Ohtake, Y.; Ikegami, S.; Hashimoto, S. Synlett 1996, 85. (f) Watanabe, N.; Ohtake, Y.; Hashimoto, S.; Shiro, M.; Ikegami, S. Tetrahedron Lett. 1995, 36, 1491.
21. For reports on enantioselective catalysis by dirhodium complexes prepared from chiral carboxylic acids, see: (a) Kennedy, M.; McKervey, M. A.; Maguire, A. R.; Roos, G. H. P. J. Chem. Soc., Chem. Comm. 1990, 361. (b) Fernandez Garcia, C.; McKervey, M. A.; Ye, T. J. Chem. Soc. Chem. Commun. 1996, 1465. (c) Davies, H. M. L.; Bruzinski, P. R.; Lake, D. H.; Kong, N.; Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6897. (d) Davies, H. M. L.; Matasi, J. J.; Hodges, L. M.; Huby, N. J. S.; Thornley, C.; Kong, N.; Houser, J. H. J. Org. Chem. 1997, 62, 1095. (e) Watanabe, N.; Ogawa, T.; Ohtake, Y.; Ikegami, S.; Hashimoto, S. Synlett 1996, 85. (f) Watanabe, N.; Ohtake, Y.; Hashimoto, S.; Shiro, M.; Ikegami, S. Tetrahedron Lett. 1995, 36, 1491.
22. (a) Cotton, F. A.; Walton, R. A. Multiple Bonds Between Metal Atoms, 2nd ed.; Oxford University Press: Oxford, 1993.
23. (b) Chakravarty, A. R.; Cotton, F. A.; Tocher, D. A.; Tocher, J. H. Organometallics 1985, 4, 8.
24. (c) The nomenclature for helicity molecules has been used: Eliel, E. L.; Wilen, S. H.; Mander, L. N. Stereochemistry of Organic Compounds; Wiley-Interscience, New York, 1994. (Formula Presented)
25. (a) Estevan, F.; Lahuerta, P.; Pérez-Prieto, J.; Sanaú, M.; Stiriba, S.-E.; Ubeda, M. A. Organometallics 1997, 16, 880.
26. (b) Estevan, F.; Lahuerta, P.; Pérez-Prieto, J.; Pereira, I.; Stiriba, S.-E. Organometallics 1998, 17, 3442.
27. Taber, D. F.; You, K. K.; Rheingold, A. L. J. Am. Chem. Soc. 1996, 118, 547.
28. N-(4-Methylphenylsulfonyl-(L)-proline was prepared following a literature procedure: Cupps, T. L.; Boutin, R. H.; Rapoport, H. J. Org. Chem. 1985, 50, 3972.
29. The separation of the diastereoisomer was performed in a 2.5 × 100 cm column using flash silica gel as support and 50:2 methylene chloride/ ethyl ether as eluent. Compound 6a was the first eluted isomer.
30. 3, Z = 4, R = 0.0832, GOF = 1.062.
31. 3CN).
32. The absolute configuration of ketone 4 was determined by correlation of the sign of the rotation of polarized light with that of the known enantiomer (ref 13). The major isomer was (S)-4 when (M)-7 was used, which was consistent with the outcome predicted in eq 2.
33. Paquette, L. A.; Gilday, J. P.; Ra, C. S. J. Am. Chem. Soc. 1987, 109, 6858.
34. The carbene derived from (M)-7 (or (P)-7) is very reactive, as evidenced by the observation that attempted cyclization of i (ref 15) gives not the cyclized product ii, but only the eliminated product iii. This suggests that the carbene derived from (M-7 would have a very early transition state (long C-C distance at the point of commitment to cyclization). While the three-dimensional shape of (M)-7 is intriguing, it will be necessary to significantly attenuate the reactivity of the derived carbene if a highly selective catalyst is to be achieved. (Formula Presented)
35. Taber, D. F.; Hennessy, M. J.; Louey, J. P. J. Org. Chem. 1992, 57, 436.