Rhodium-catalyzed asymmetric synthesis of indanones: Development of a new "axially chiral" bisphosphine ligand

Journal of the American Chemical Society

Volumn 128, Issue 9, 2006, Pages 2772-2773

  Shintani, Ryo ^a   Yashio, Keiji ^a   Nakamura, Tomoaki ^a   Okamoto, Kazuhiro ^a   Shimada, Toyoshi ^a   Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

INDANONE DERIVATIVE; PHOSPHINE DERIVATIVE; RHODIUM;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHIRALITY; COMPLEX FORMATION; ENANTIOMER; ENANTIOSELECTIVITY; RACEMIC MIXTURE; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 33644961282     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja056584s     Document Type: Article

References (31)

1. (a) Ojima, I., Ed. Catalytic Asymmetric Synthesis, 2nd ed.; Wiley-VCH: New York, 2000.
2. (b) Jacobsen, E. N., Pfaltz, A., Yamamoto, H., Eds. Comprehensive Asymmetric Catalysis I-III; Springer-Verlag: New York, 1999.
3. For recent reviews on modified binap ligands, see: (a) Shimizu, H.; Nagasaki, I.; Saito, T. Tetrahedron 2005, 61, 5405.
4. (b) Berthod, M.; Mignani, G.; Woodward, G.; Lemaire, M. Chem. Rev. 2005, 105, 1801.
5. Takaya, H.; Mashima, K.; Koyano, K.; Yagi, M.; Kumobayashi, H.; Taketomi, T.; Akutagawa, S.; Noyori, R. J. Org. Chem. 1986, 51, 629.
6. For examples of correlations between enantiomeric excesses in asymmetric catalysis and dihedral angles of the ligands, see: (a) Jeulin, S.; Duprat de Paule, S.; Ratovelomanana-Vidal, V.; Genêt, J.-P.; Champion, N.; Dellis, P. Angew. Chem., Int. Ed. 2004, 43, 320.
7. (b) Zhang, Z.; Qian, H.; Longmire, J.; Zhang, X. J. Org. Chem. 2000, 65, 6223.
8. See also: (c) Aikawa, K.; Kainuma, S.; Hatano, M.; Mikami, K. Tetrahedron Lett. 2004, 45, 183.
9. (a) Shintani, R.; Okamoto, K.; Hayashi, T. J. Am. Chem. Soc. 2005, 127, 2872.
10. (b) Yamabe, H.; Mizuno, A.; Kusama, H.; Iwasawa, N. J. Am. Chem. Soc. 2005, 127, 3248.
11. For recent examples of catalytic asymmetric synthesis of β-chiral indanones, see: (a) Yun, J.; Buchwald, S. L. J. Org. Chem. 2000, 65, 767.
12. (b) Caro, Y.; Torrado, M.; Masaguer, C. F.; Ravina, E. Tetrahedron: Asymmetry 2003, 14, 3689.
13. (c) Kumagai, N.; Matsunaga, S.; Shibasaki, M. Org. Lett. 2001, 3, 4251.
14. (d) Arp, F. O.; Fu, G. C. J. Am. Chem. Soc. 2005, 127, 10482.
15. (e) Kundu, K.; McCullagh, J. V.; Morehead, A. T., Jr. J. Am. Chem. Soc. 2005, 127, 16042.
16. Schmid, R.; Foricher, J.; Cereghetti, M.; Schönholzer, P. Helv. Chim. Acta 1991, 74, 370.
17. There are no literature data of the dihedral angles of MeO-biphep and segphos in rhodium complexes. For the dihedral angle of binap in a rhodium complex (74.4°), see: Toriumi, K.; Ito, T.; Takaya, H.; Souchi, T.; Noyori, R. Acta Crystallogr., Sect. B 1982, 38, 807.
18. Saito, T.; Yokozawa, T.; Ishizaki, T.; Moroi, T.; Sayo, N.; Miura, T.; Kumobayashi, H. Adv. Synth. Catal. 2001, 343, 264.
19. Zhang, X.; Mashima, K.; Koyano, K.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Takaya, H. Tetrahedron Lett. 1991, 32, 7283.
20. Zhang, X.; Mashima, K.; Koyano, K.; Sayo, N.; Kumobayashi, H.; Akutagawa, S.; Takaya, H. J. Chem. Soc., Perkin Trans. 1 1994, 2309.
21. Hayashi, T. Acc. Chem. Res. 2000, 33, 354.
22. For examples of the axial chirality control of tropos ligands by complexing to a transition metal with an enantiopure chiral ligand, see: (a) Mikami, K.; Korenaga, T.; Terada, M.; Ohkuma, T.; Pham, T.; Noyori, R. Angew. Chem., Int. Ed. 1999, 38, 495.
23. (b) Mikami, K.; Aikawa, K.; Korenaga, T. Org. Lett. 2001, 3, 243.
24. (c) Tudor, M. D.; Becker, J. J.; White, P. S.; Gagné, M. R. Organometallics 2000, 19, 4376.
25. Uozumi, Y.; Tanahashi, A.; Lee, S.-Y.; Hayashi, T. J. Org. Chem. 1993, 58, 1945.
26. (a) Schaub, B.; Jenny, T.; Schlosser, M. Tetrahedron Lett. 1984, 25, 4097.
27. (b) Gray, M.; Chapell, B. J.; Felding, J.; Taylor, N. J.; Snieckus, V. Synlett 1998, 422.
28. See ref 10c.
29. See also: (d) Hartung, C. G.; Snieckus, V. In Modern Arene Chemistry; Astruc, D., Ed.; Wiley-VCH: Weinheim, Germany, 2002; p 330.
30. 4 and then desilylation with TBAF (see Supporting Information for details).
31. In the reaction of rac-substrates, (R)-isomer must also be isomerized to indanone to some extent since the yields are typically >50% (Table 1).