Preparation of bi- and tridentate doubly P-chiral diphosphine dioxide ligands for asymmetric catalysis

Tetrahedron Letters

Volumn 37, Issue 27, 1996, Pages 4733-4736

  Lam, William W L ^a   Haynes, Richard K ^a   Yeung, Lam Lung ^a   Chan, Eric W K ^a  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHINE DERIVATIVE;

ARTICLE; CATALYSIS; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030199621     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00953-7     Document Type: Article

References (23)

1. 1. Takaya, H.; Ohta, T.; and Noyori, R. In Catalytic Asymmetric Synthesis, Ojima, I., Ed.; VCH Publishers, 1993, Ch. 1; Noyori, R. In Asymmetric Catalysis In Organic Synthesis, Noyori, R., Ed.; John Wiley & Sons, 1994.
2. 1. Takaya, H.; Ohta, T.; and Noyori, R. In Catalytic Asymmetric Synthesis, Ojima, I., Ed.; VCH Publishers, 1993, Ch. 1; Noyori, R. In Asymmetric Catalysis In Organic Synthesis, Noyori, R., Ed.; John Wiley & Sons, 1994.
3. 2. Pietrusiewicz, K. M.; and Zablocka, M Chem. Rev. 1994, 94, 1300.
4. 3. Vineyard, B. D.; Knowles, W. S.; Sachman, G. L.; Weinkauff, D. J. J Am. Chem. Soc. 1977, 99, 5946.
5. 4. Juge, S.; Stephen, M.; Lafitte, J. A.; Genet, J.-P. Tetrahedron Lett. 1990, 31, 6357; Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc. 1990, 112, 5244; Corey, E. J.; Chen, Z. L.; Tenoury, G. J. J. Am. Chem. Soc. 1993, 115, 11000; Carey, J. V.; Barker, M. D.; Brown, J. M.; Russell, M. J. Chem. Soc., Perkin Trans 1, 1993, 831;
6. 4. Juge, S.; Stephen, M.; Lafitte, J. A.; Genet, J.-P. Tetrahedron Lett. 1990, 31, 6357; Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc. 1990, 112, 5244; Corey, E. J.; Chen, Z. L.; Tenoury, G. J. J. Am. Chem. Soc. 1993, 115, 11000; Carey, J. V.; Barker, M. D.; Brown, J. M.; Russell, M. J. Chem. Soc., Perkin Trans 1, 1993, 831;
7. 4. Juge, S.; Stephen, M.; Lafitte, J. A.; Genet, J.-P. Tetrahedron Lett. 1990, 31, 6357; Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc. 1990, 112, 5244; Corey, E. J.; Chen, Z. L.; Tenoury, G. J. J. Am. Chem. Soc. 1993, 115, 11000; Carey, J. V.; Barker, M. D.; Brown, J. M.; Russell, M. J. Chem. Soc., Perkin Trans 1, 1993, 831;
8. 4. Juge, S.; Stephen, M.; Lafitte, J. A.; Genet, J.-P. Tetrahedron Lett. 1990, 31, 6357; Imamoto, T.; Oshiki, T.; Onozawa, T.; Kusumoto, T.; Sato, K. J. Am. Chem. Soc. 1990, 112, 5244; Corey, E. J.; Chen, Z. L.; Tenoury, G. J. J. Am. Chem. Soc. 1993, 115, 11000; Carey, J. V.; Barker, M. D.; Brown, J. M.; Russell, M. J. Chem. Soc., Perkin Trans 1, 1993, 831;
9. Ramsden, J. A.; Brown, J. M.; Hursthouse, M. B.; Karalulov, A. I. Tetrahedron Asymmetry 1994, 5, 2033;
10. Muci, A. R.; Campos, K. R.; Evans, D. A. J. Am. Chem. Soc. 1995, 117, 9075.
11. 5. Haynes, R. K.; Freeman, R. N.; Mitchell, C. R.; Vonwiller, S. C. J. Org. Chem. 1994, 59, 2919.
12. 6. All new compounds were characterized by spectroscopic methods and elemental analysis and/or accurate mass spectra.
13. 7. Reduction of the diphosphine dioxides to phosphines, formation of phosphine Rh-complexes and uses in asymmetric hydrogenation will be reported elsewhere.
14. 8. In contrast, enantiomericaly pure tert-butyl(o-anisyl)phosphine-borane and related compounds react both with primary and secondary alkyl halides, also without loss of stereochemical integrity: Imamoto, T.; Oshiki, T.; Onozawa, T.; Matsuo, T.; Hikosaka, M.; Yanagawa, M. Heteroatom Chem. 1992, 3, 563; Imamoto, T.; Matsuo, M.; Nonomura, T.; Kisjikawa, K.; Yanagawa, M. Heteroatom Chem. 1993, 4, 475.
15. 8. In contrast, enantiomericaly pure tert-butyl(o-anisyl)phosphine-borane and related compounds react both with primary and secondary alkyl halides, also without loss of stereochemical integrity: Imamoto, T.; Oshiki, T.; Onozawa, T.; Matsuo, T.; Hikosaka, M.; Yanagawa, M. Heteroatom Chem. 1992, 3, 563; Imamoto, T.; Matsuo, M.; Nonomura, T.; Kisjikawa, K.; Yanagawa, M. Heteroatom Chem. 1993, 4, 475.
16. 2 according to a procedure used for oxidative coupling of anions: Minami, T.; Okada, Y.; Nomura, S.; Hirota, S.; Nagahara, Y. and Fukuyama, K. Chem. Lett. 1986, 4, 613. Whilst formation of the desired product did take place, it was not possible to bring the reaction to completion, or to separate the trans-cyclohexyl-1,2-diphosphine dioxide from the unreacted open-chain diphosphine dioxide.
17. 2 according to a procedure used for oxidative coupling of anions: Minami, T.; Okada, Y.; Nomura, S.; Hirota, S.; Nagahara, Y. and Fukuyama, K. Chem. Lett. 1986, 4, 613. Whilst formation of the desired product did take place, it was not possible to bring the reaction to completion, or to separate the trans-cyclohexyl-1,2-diphosphine dioxide from the unreacted open-chain diphosphine dioxide.
18. 2 according to a procedure used for oxidative coupling of anions: Minami, T.; Okada, Y.; Nomura, S.; Hirota, S.; Nagahara, Y. and Fukuyama, K. Chem. Lett. 1986, 4, 613. Whilst formation of the desired product did take place, it was not possible to bring the reaction to completion, or to separate the trans-cyclohexyl-1,2-diphosphine dioxide from the unreacted open-chain diphosphine dioxide.
19. p)-isomer, while with 0.4 equiv. of diiodide, secondary phosphine oxide with 66% ee was recovered.
20. 11. Pietrusiewicz, K. M.; Zablocka, M. Tetrahedron Lett. 1988, 29, 1991; Pietrusiewicz, K. M.; Wisniewski, W.; Zablocka, M. Tetrahedron 1989, 45, 337.
21. 11. Pietrusiewicz, K. M.; Zablocka, M. Tetrahedron Lett. 1988, 29, 1991; Pietrusiewicz, K. M.; Wisniewski, W.; Zablocka, M. Tetrahedron 1989, 45, 337.
22. p)-tert-Butylphenylphosphinobromidate 6 is enantiomerically pure, as established by NMR assay at 400 MHz with tert-butylphenylphosphinothioic acid according to the method described in ref. 5. The bromidate been reported previously, but with substantially lower optical rotation: see Omelanczuk, J.; Mikolajczyk, M. J. Chem. Soc., Chem. Commun. 1994, 2223.
23. 13. The absolute configuration of compound 10 is secured by X-ray crystallography; details may be obtained from the authors. Thus, displacement of bromide from bromidate 6 by amine proceeds with clean inversion, in contrast to an apparently stereoretentive outcome with thiolate as described in the paper quoted in ref. 12.