Racemic but tropos (chirally flexible) BIPHEP ligands for Rh(I)-complexes: Highly enantioselective ene-type cyclization of 1,6-enynes

Organic Letters

Volumn 6, Issue 21, 2004, Pages 3699-3701

  Mikami, Koichi ^a   Kataoka, Shohei ^a   Yusa, Yukinori ^a   Aikawa, Kohsuke ^a  

^a Tokyo Institute of Technology ^*  (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

LIGAND;

ARTICLE; CATALYSIS; CHIRALITY; CYCLIZATION; ENANTIOSELECTIVITY; LIGAND BINDING; RACEMIZATION; RIGIDITY; ROOM TEMPERATURE; SYNTHESIS;

EID: 7244257816     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol048604l     Document Type: Article

References (25)

1. Mikami, K.; Aikawa, K.; Yusa, Y.; Jodry, J. J.; Yamanaka, M. Synlett 2002, 10, 1561-1578.
2. Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H. Comprehensive Asymmetric Catalysis; Springer: Berlin, 1999; Vols. 1-3.
3. The activation barrier to axial torsion in selectivity deuterated BIPHEP is measured to be only (22 ± 1) kcal, which suggests that axial rotation takes place at room temperature or above: Desponds, O.; Schlosser, M. Tetradedron Lett. 1996, 37, 47-48.
4. For the BIPHEP-Ru complex: (a) Mikami, K.; Korenaga, T.; Terada, M.; Ohkuma, T.; Pham, T.; Noyori, R. Angew. Chem., Int. Ed. 1999, 38, 495-497. For the BIPHEP-Pd complex: (b) Mikami, K.; Aikawa, K.; Yusa, Y.; Hatano, M. Org. Lett. 2002, 4, 91-94. (c) Mikami, K.; Aikawa, K.; Yusa, Y. Org. Lett. 2002, 4, 95-97. For the BIPHEP-Pt complex: (d) Tudor, M. D.; Becker, J. J.; White, P. S.; Gagné, M. R. Organometallics 2000, 19, 4376-4484. (e) Becker, J. J.; White, P. S.; Gagné, M. R. J. Am. Chem. Soc. 2001, 123, 9478-9479.
5. For the BIPHEP-Ru complex: (a) Mikami, K.; Korenaga, T.; Terada, M.; Ohkuma, T.; Pham, T.; Noyori, R. Angew. Chem., Int. Ed. 1999, 38, 495-497. For the BIPHEP-Pd complex: (b) Mikami, K.; Aikawa, K.; Yusa, Y.; Hatano, M. Org. Lett. 2002, 4, 91-94. (c) Mikami, K.; Aikawa, K.; Yusa, Y. Org. Lett. 2002, 4, 95-97. For the BIPHEP-Pt complex: (d) Tudor, M. D.; Becker, J. J.; White, P. S.; Gagné, M. R. Organometallics 2000, 19, 4376-4484. (e) Becker, J. J.; White, P. S.; Gagné, M. R. J. Am. Chem. Soc. 2001, 123, 9478-9479.
6. For the BIPHEP-Ru complex: (a) Mikami, K.; Korenaga, T.; Terada, M.; Ohkuma, T.; Pham, T.; Noyori, R. Angew. Chem., Int. Ed. 1999, 38, 495-497. For the BIPHEP-Pd complex: (b) Mikami, K.; Aikawa, K.; Yusa, Y.; Hatano, M. Org. Lett. 2002, 4, 91-94. (c) Mikami, K.; Aikawa, K.; Yusa, Y. Org. Lett. 2002, 4, 95-97. For the BIPHEP-Pt complex: (d) Tudor, M. D.; Becker, J. J.; White, P. S.; Gagné, M. R. Organometallics 2000, 19, 4376-4484. (e) Becker, J. J.; White, P. S.; Gagné, M. R. J. Am. Chem. Soc. 2001, 123, 9478-9479.
7. For the BIPHEP-Ru complex: (a) Mikami, K.; Korenaga, T.; Terada, M.; Ohkuma, T.; Pham, T.; Noyori, R. Angew. Chem., Int. Ed. 1999, 38, 495-497. For the BIPHEP-Pd complex: (b) Mikami, K.; Aikawa, K.; Yusa, Y.; Hatano, M. Org. Lett. 2002, 4, 91-94. (c) Mikami, K.; Aikawa, K.; Yusa, Y. Org. Lett. 2002, 4, 95-97. For the BIPHEP-Pt complex: (d) Tudor, M. D.; Becker, J. J.; White, P. S.; Gagné, M. R. Organometallics 2000, 19, 4376-4484. (e) Becker, J. J.; White, P. S.; Gagné, M. R. J. Am. Chem. Soc. 2001, 123, 9478-9479.
8. For the BIPHEP-Ru complex: (a) Mikami, K.; Korenaga, T.; Terada, M.; Ohkuma, T.; Pham, T.; Noyori, R. Angew. Chem., Int. Ed. 1999, 38, 495-497. For the BIPHEP-Pd complex: (b) Mikami, K.; Aikawa, K.; Yusa, Y.; Hatano, M. Org. Lett. 2002, 4, 91-94. (c) Mikami, K.; Aikawa, K.; Yusa, Y. Org. Lett. 2002, 4, 95-97. For the BIPHEP-Pt complex: (d) Tudor, M. D.; Becker, J. J.; White, P. S.; Gagné, M. R. Organometallics 2000, 19, 4376-4484. (e) Becker, J. J.; White, P. S.; Gagné, M. R. J. Am. Chem. Soc. 2001, 123, 9478-9479.
9. A half-life of 1000 s (16.7 min) is considered as the minimum requirement for atropos molecules; cf. Oki, M. Top. Stereochem. 1983, 14, 1-81.
10. 2 was based on 12097 observed reflections and 542 variable parameters and converged to R = 0.076 and Rw = 0.179. Goodness of fit = 1.084, shift/ error = 0.006. Crystallographic data (excluding structure factors) for the structure reported in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-241306. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB21EZ, U.K. Fax: (+44)1223-336-033; E-mail: deposit@ccdc.cam.ac.uk.
11. For the BINAP-Rh complex: Takaya, H.; Miyashita, A.; Souchi, T.; Noyori, R. Tetrahedron 1984, 40, 1245-1253. For the X-ray analysis of DPPE-Rh complex: Halpern, J.; Rily, D. P.; Chan, A. S. C.; Pluth, J. J. J. Am. Chem. Soc. 1977, 8055-8057.
12. For the BINAP-Rh complex: Takaya, H.; Miyashita, A.; Souchi, T.; Noyori, R. Tetrahedron 1984, 40, 1245-1253. For the X-ray analysis of DPPE-Rh complex: Halpern, J.; Rily, D. P.; Chan, A. S. C.; Pluth, J. J. J. Am. Chem. Soc. 1977, 8055-8057.
13. 2) δ 42.7 (dd, J = 195.5, 43.6 Hz), 46.4 (dd, J = 211.4, 43.6 Hz).
14. For reviews on ene-type cycloisomerization: (a) Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42. (b) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. (c) Trost, B. M. Chem. Eur. J. 1998, 4, 2405-2412. (d) Trost, B. M.; Krische, M. J. Synlett 1998, 1-16. (e) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813-834. (f) Mendez, M.; Victor, M.; Fürstner, A. Chemtracts Org. Chem. 2003, 16, 397-425. (g) He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198-8199. (h) Lei, A.; He, M.; Wu, S.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 3457-3460. (i) Lei, A.; Waldkirch, J. P.; He, M.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 4526-4529. (j) Mikami, K.; Hatano, M. Proc. Natl. Acad. Sci. U.S.A. 2004, 20, 5767-5769. (k) Hatano, M.; Mikami, K. J. Am. Chem Soc. 2003, 125, 4704-4705. (l) Mikami, K.; Yusa, Y.; Hatano, M.; Wakabayasi, K.; Aikawa, K. Chem. Commun. 2004, 98-99.
15. For reviews on ene-type cycloisomerization: (a) Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42. (b) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. (c) Trost, B. M. Chem. Eur. J. 1998, 4, 2405-2412. (d) Trost, B. M.; Krische, M. J. Synlett 1998, 1-16. (e) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813-834. (f) Mendez, M.; Victor, M.; Fürstner, A. Chemtracts Org. Chem. 2003, 16, 397-425. (g) He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198-8199. (h) Lei, A.; He, M.; Wu, S.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 3457-3460. (i) Lei, A.; Waldkirch, J. P.; He, M.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 4526-4529. (j) Mikami, K.; Hatano, M. Proc. Natl. Acad. Sci. U.S.A. 2004, 20, 5767-5769. (k) Hatano, M.; Mikami, K. J. Am. Chem Soc. 2003, 125, 4704-4705. (l) Mikami, K.; Yusa, Y.; Hatano, M.; Wakabayasi, K.; Aikawa, K. Chem. Commun. 2004, 98-99.
16. For reviews on ene-type cycloisomerization: (a) Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42. (b) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. (c) Trost, B. M. Chem. Eur. J. 1998, 4, 2405-2412. (d) Trost, B. M.; Krische, M. J. Synlett 1998, 1-16. (e) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813-834. (f) Mendez, M.; Victor, M.; Fürstner, A. Chemtracts Org. Chem. 2003, 16, 397-425. (g) He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198-8199. (h) Lei, A.; He, M.; Wu, S.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 3457-3460. (i) Lei, A.; Waldkirch, J. P.; He, M.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 4526-4529. (j) Mikami, K.; Hatano, M. Proc. Natl. Acad. Sci. U.S.A. 2004, 20, 5767-5769. (k) Hatano, M.; Mikami, K. J. Am. Chem Soc. 2003, 125, 4704-4705. (l) Mikami, K.; Yusa, Y.; Hatano, M.; Wakabayasi, K.; Aikawa, K. Chem. Commun. 2004, 98-99.
17. For reviews on ene-type cycloisomerization: (a) Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42. (b) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. (c) Trost, B. M. Chem. Eur. J. 1998, 4, 2405-2412. (d) Trost, B. M.; Krische, M. J. Synlett 1998, 1-16. (e) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813-834. (f) Mendez, M.; Victor, M.; Fürstner, A. Chemtracts Org. Chem. 2003, 16, 397-425. (g) He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198-8199. (h) Lei, A.; He, M.; Wu, S.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 3457-3460. (i) Lei, A.; Waldkirch, J. P.; He, M.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 4526-4529. (j) Mikami, K.; Hatano, M. Proc. Natl. Acad. Sci. U.S.A. 2004, 20, 5767-5769. (k) Hatano, M.; Mikami, K. J. Am. Chem Soc. 2003, 125, 4704-4705. (l) Mikami, K.; Yusa, Y.; Hatano, M.; Wakabayasi, K.; Aikawa, K. Chem. Commun. 2004, 98-99.
18. For reviews on ene-type cycloisomerization: (a) Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42. (b) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. (c) Trost, B. M. Chem. Eur. J. 1998, 4, 2405-2412. (d) Trost, B. M.; Krische, M. J. Synlett 1998, 1-16. (e) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813-834. (f) Mendez, M.; Victor, M.; Fürstner, A. Chemtracts Org. Chem. 2003, 16, 397-425. (g) He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198-8199. (h) Lei, A.; He, M.; Wu, S.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 3457-3460. (i) Lei, A.; Waldkirch, J. P.; He, M.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 4526-4529. (j) Mikami, K.; Hatano, M. Proc. Natl. Acad. Sci. U.S.A. 2004, 20, 5767-5769. (k) Hatano, M.; Mikami, K. J. Am. Chem Soc. 2003, 125, 4704-4705. (l) Mikami, K.; Yusa, Y.; Hatano, M.; Wakabayasi, K.; Aikawa, K. Chem. Commun. 2004, 98-99.
19. For reviews on ene-type cycloisomerization: (a) Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42. (b) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. (c) Trost, B. M. Chem. Eur. J. 1998, 4, 2405-2412. (d) Trost, B. M.; Krische, M. J. Synlett 1998, 1-16. (e) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813-834. (f) Mendez, M.; Victor, M.; Fürstner, A. Chemtracts Org. Chem. 2003, 16, 397-425. (g) He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198-8199. (h) Lei, A.; He, M.; Wu, S.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 3457-3460. (i) Lei, A.; Waldkirch, J. P.; He, M.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 4526-4529. (j) Mikami, K.; Hatano, M. Proc. Natl. Acad. Sci. U.S.A. 2004, 20, 5767-5769. (k) Hatano, M.; Mikami, K. J. Am. Chem Soc. 2003, 125, 4704-4705. (l) Mikami, K.; Yusa, Y.; Hatano, M.; Wakabayasi, K.; Aikawa, K. Chem. Commun. 2004, 98-99.
20. For reviews on ene-type cycloisomerization: (a) Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42. (b) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. (c) Trost, B. M. Chem. Eur. J. 1998, 4, 2405-2412. (d) Trost, B. M.; Krische, M. J. Synlett 1998, 1-16. (e) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813-834. (f) Mendez, M.; Victor, M.; Fürstner, A. Chemtracts Org. Chem. 2003, 16, 397-425. (g) He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198-8199. (h) Lei, A.; He, M.; Wu, S.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 3457-3460. (i) Lei, A.; Waldkirch, J. P.; He, M.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 4526-4529. (j) Mikami, K.; Hatano, M. Proc. Natl. Acad. Sci. U.S.A. 2004, 20, 5767-5769. (k) Hatano, M.; Mikami, K. J. Am. Chem Soc. 2003, 125, 4704-4705. (l) Mikami, K.; Yusa, Y.; Hatano, M.; Wakabayasi, K.; Aikawa, K. Chem. Commun. 2004, 98-99.
21. For reviews on ene-type cycloisomerization: (a) Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42. (b) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. (c) Trost, B. M. Chem. Eur. J. 1998, 4, 2405-2412. (d) Trost, B. M.; Krische, M. J. Synlett 1998, 1-16. (e) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813-834. (f) Mendez, M.; Victor, M.; Fürstner, A. Chemtracts Org. Chem. 2003, 16, 397-425. (g) He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198-8199. (h) Lei, A.; He, M.; Wu, S.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 3457-3460. (i) Lei, A.; Waldkirch, J. P.; He, M.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 4526-4529. (j) Mikami, K.; Hatano, M. Proc. Natl. Acad. Sci. U.S.A. 2004, 20, 5767-5769. (k) Hatano, M.; Mikami, K. J. Am. Chem Soc. 2003, 125, 4704-4705. (l) Mikami, K.; Yusa, Y.; Hatano, M.; Wakabayasi, K.; Aikawa, K. Chem. Commun. 2004, 98-99.
22. For reviews on ene-type cycloisomerization: (a) Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42. (b) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. (c) Trost, B. M. Chem. Eur. J. 1998, 4, 2405-2412. (d) Trost, B. M.; Krische, M. J. Synlett 1998, 1-16. (e) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813-834. (f) Mendez, M.; Victor, M.; Fürstner, A. Chemtracts Org. Chem. 2003, 16, 397-425. (g) He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198-8199. (h) Lei, A.; He, M.; Wu, S.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 3457-3460. (i) Lei, A.; Waldkirch, J. P.; He, M.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 4526-4529. (j) Mikami, K.; Hatano, M. Proc. Natl. Acad. Sci. U.S.A. 2004, 20, 5767-5769. (k) Hatano, M.; Mikami, K. J. Am. Chem Soc. 2003, 125, 4704-4705. (l) Mikami, K.; Yusa, Y.; Hatano, M.; Wakabayasi, K.; Aikawa, K. Chem. Commun. 2004, 98-99.
23. For reviews on ene-type cycloisomerization: (a) Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42. (b) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. (c) Trost, B. M. Chem. Eur. J. 1998, 4, 2405-2412. (d) Trost, B. M.; Krische, M. J. Synlett 1998, 1-16. (e) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813-834. (f) Mendez, M.; Victor, M.; Fürstner, A. Chemtracts Org. Chem. 2003, 16, 397-425. (g) He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198-8199. (h) Lei, A.; He, M.; Wu, S.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 3457-3460. (i) Lei, A.; Waldkirch, J. P.; He, M.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 4526-4529. (j) Mikami, K.; Hatano, M. Proc. Natl. Acad. Sci. U.S.A. 2004, 20, 5767-5769. (k) Hatano, M.; Mikami, K. J. Am. Chem Soc. 2003, 125, 4704-4705. (l) Mikami, K.; Yusa, Y.; Hatano, M.; Wakabayasi, K.; Aikawa, K. Chem. Commun. 2004, 98-99.
24. For reviews on ene-type cycloisomerization: (a) Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42. (b) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. (c) Trost, B. M. Chem. Eur. J. 1998, 4, 2405-2412. (d) Trost, B. M.; Krische, M. J. Synlett 1998, 1-16. (e) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813-834. (f) Mendez, M.; Victor, M.; Fürstner, A. Chemtracts Org. Chem. 2003, 16, 397-425. (g) He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198-8199. (h) Lei, A.; He, M.; Wu, S.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 3457-3460. (i) Lei, A.; Waldkirch, J. P.; He, M.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 4526-4529. (j) Mikami, K.; Hatano, M. Proc. Natl. Acad. Sci. U.S.A. 2004, 20, 5767-5769. (k) Hatano, M.; Mikami, K. J. Am. Chem Soc. 2003, 125, 4704-4705. (l) Mikami, K.; Yusa, Y.; Hatano, M.; Wakabayasi, K.; Aikawa, K. Chem. Commun. 2004, 98-99.
25. For reviews on ene-type cycloisomerization: (a) Trost, B. M. Acc. Chem. Res. 1990, 23, 34-42. (b) Ojima, I.; Tzamarioudaki, M.; Li, Z.; Donovan, R. J. Chem. Rev. 1996, 96, 635-662. (c) Trost, B. M. Chem. Eur. J. 1998, 4, 2405-2412. (d) Trost, B. M.; Krische, M. J. Synlett 1998, 1-16. (e) Aubert, C.; Buisine, O.; Malacria, M. Chem. Rev. 2002, 102, 813-834. (f) Mendez, M.; Victor, M.; Fürstner, A. Chemtracts Org. Chem. 2003, 16, 397-425. (g) He, M.; Zhang, X. J. Am. Chem. Soc. 2002, 124, 8198-8199. (h) Lei, A.; He, M.; Wu, S.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 3457-3460. (i) Lei, A.; Waldkirch, J. P.; He, M.; Zhang, X. Angew. Chem., Int. Ed. 2002, 41, 4526-4529. (j) Mikami, K.; Hatano, M. Proc. Natl. Acad. Sci. U.S.A. 2004, 20, 5767-5769. (k) Hatano, M.; Mikami, K. J. Am. Chem Soc. 2003, 125, 4704-4705. (l) Mikami, K.; Yusa, Y.; Hatano, M.; Wakabayasi, K.; Aikawa, K. Chem. Commun. 2004, 98-99.