Optically active 1,1′-Di-tert-butyl-2,2′-diphosphetanyl and its application in rhodium-catalyzed asymmetric hydrogenations

Synthesis

Volumn , Issue 9, 2004, Pages 1353-1358

  Imamoto, Tsuneo ^a   Oohara, Nobuhiko ^b   Takahashi, Hidetoshi ^a  

^a CHIBA UNIVERSITY   (Japan)

^b Nippon Chemiphar Co Ltd   (Japan)

Author keywords

Asymmetric hydrogenation; Chiral phosphetane derivative; Chiral phosphine ligand; Phosphine borane; Rhodium complex

Indexed keywords

CATALYSTS; OPTICAL ENGINEERING; RHODIUM; SYNTHESIS (CHEMICAL);

BORANES; LIGAND;

HYDROGENATION;

ACETIC ACID DERIVATIVE; ACRYLIC ACID DERIVATIVE; BORANE DERIVATIVE; PHOSPHINE DERIVATIVE; RHODIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHIRALITY; HYDROGENATION; LIGAND BINDING; QUANTITATIVE ANALYSIS;

EID: 3042716629     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-822396     Document Type: Article

References (33)

1. For representative reviews and accounts, see: (a) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029. (b) Crépy, K. V. L.; Imamoto, T. Top. Curr. Chem. 2003, 229, 1. (c) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: Weinheim, 2000, Chap. 1. (d) Brown, J. M. In Comprehensive Asymmetric Catalysis, Vol. 1; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, Chap. 5.1. (e) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
2. For representative reviews and accounts, see: (a) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029. (b) Crépy, K. V. L.; Imamoto, T. Top. Curr. Chem. 2003, 229, 1. (c) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: Weinheim, 2000, Chap. 1. (d) Brown, J. M. In Comprehensive Asymmetric Catalysis, Vol. 1; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, Chap. 5.1. (e) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
3. For representative reviews and accounts, see: (a) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029. (b) Crépy, K. V. L.; Imamoto, T. Top. Curr. Chem. 2003, 229, 1. (c) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: Weinheim, 2000, Chap. 1. (d) Brown, J. M. In Comprehensive Asymmetric Catalysis, Vol. 1; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, Chap. 5.1. (e) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
4. For representative reviews and accounts, see: (a) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029. (b) Crépy, K. V. L.; Imamoto, T. Top. Curr. Chem. 2003, 229, 1. (c) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: Weinheim, 2000, Chap. 1. (d) Brown, J. M. In Comprehensive Asymmetric Catalysis, Vol. 1; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, Chap. 5.1. (e) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
5. For representative reviews and accounts, see: (a) Tang, W.; Zhang, X. Chem. Rev. 2003, 103, 3029. (b) Crépy, K. V. L.; Imamoto, T. Top. Curr. Chem. 2003, 229, 1. (c) Ohkuma, T.; Kitamura, M.; Noyori, R. In Catalytic Asymmetric Synthesis, 2nd ed.; Ojima, I., Ed.; Wiley-VCH: Weinheim, 2000, Chap. 1. (d) Brown, J. M. In Comprehensive Asymmetric Catalysis, Vol. 1; Jacobsen, E. N.; Pfaltz, A.; Yamamoto, H., Eds.; Springer: Berlin, 1999, Chap. 5.1. (e) Noyori, R. Asymmetric Catalysis in Organic Synthesis; Wiley: New York, 1994.
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11. Crépy, K. V. L.; Imamoto, T. Adv. Synth. Catal. 2003, 345, 79.
12. Gridnev, I. D.; Imamoto, T. Acc. Chem. Res. in press.
13. (a) Various optically active phosphetane ligands have been reported. However, to our knowledge, P-stereogenic phosphetane ligands have been rarely synthesized
14. (b) See: Marinetti, A.; Jus, S.; Genet, J.-P. Tetrahedron Lett 1999, 40, 8365.
15. (c) See also: Berens, U.; Burk, M. J.; Gerlach, A.; Hems, W. Angew. Chem. Int. Ed. 2000, 39, 1981.
16. (d) See also: Marinetti, A.; Carmichael, D. Chem. Rev. 2002, 102, 201; and references cited therein.
17. (a) DiSquareP* closely resembles TangPhos (optically active 1,1′-di-tert-butyl-2,2′-diphosphoranyl) which has proved to be an outstanding phosphine ligand in transition metal-catalyzed asymmetric reactions
18. (b) See: Tang, W.; Zhang, X. Angew. Chem. Int. Ed. 2002, 41, 1612.
19. (c) See also: Tang, W.; Zhang, X. Org. Lett. 2002, 4, 4159.
20. (d) See also: Tang, W.; Zhang, X. Org. Lett. 2003, 5, 205.
21. (a) We independently attempted to prepare optically active 1,1′-di-tert-butyl-2,2′-diphosphoranyl using 1-tert- butylphospholane-borane. However, the deprotonation of 1-tert-butylphospholane- borane with sec-BuLi/(-)-sparteine complex proceeded with very low enantioselectivity and only (1S,1′R,2R,2′S)-1,1′-di-tert- butyl-2,2′-diphosphoranylborane was isolated as an oxidatively coupled product.
22. (b) See: Ohhashi, A.; Imamoto, T. Acta Crystallogr. Sect. C 2000, 56, 723.
23. (a) Imamoto, T.; Kusumoto, T.; Suzuki, N.; Sato, K. J. Am. Chem, Soc. 1985, 107, 5301.
24. (b) Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc. 1990, 112, 5244.
25. (c) Imamoto, T. Pure Appl. Chem. 1993, 65, 655.
26. Muci, A. R.; Campos, K. R.; Evans, D. A. J. Am. Chem. Soc. 1995, 117, 9075.
27. (a) McKinstry, L.; Livinghouse, T. Tetrahedron Lett. 1994, 35, 9319.
28. (b) McKinstry, L.; Livinghouse, T. Tetrahedron 1994, 50, 6145.
29. 4: 52.15, H, 8.75. Found: C, 51.83; H, 8.79) which was less soluble than enantiomerically pure 8.
30. (a) This type of reverse stereoselectivity was previously observed when DuPhos, BisP*, and MiniPHOS were used as the ligand
31. (b) See: Burk, M. J.; Casy, G.; Johnson, N. B. J. Org. Chem. 1998, 63, 6084.
32. (c) See also: Gridnev, I. D.; Higashi, N.; Imamoto, T. J. Am. Chem. Soc. 2000, 122, 10486.
33. (d) See also: Ref. 6.