Enantioselective synthesis of novel enantiopure phosphines via reaction of a tricarbonyl(η6-arene)chromium complex with a chiral lithium amide base

Synlett

Volumn , Issue 12, 1997, Pages 1453-1455

  Ariffin, Azhar ^a   Blake, Alexander J ^a   Li, Wan Sheung ^a   Simpkins, Nigel S ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003145073     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1061     Document Type: Article

References (21)

1. For recent reviews, See (a) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley and Sons: New York, 1994.
2. (b) Advanced Asymmetric Synthesis; Stephenson, R., Ed., Blackie Academic and Professional: London, 1996.
3. (c) Catalytic Asymmetric Synthesis; Ojima, I., Ed., VCH Publishers Inc., 1993. For more complete listings, see the bibliographies in references 2a-d.
4. 2-symmetric bis-phosphine synthesis,see (a) Longmire, J. M.; Zhang, X. Tetrahedron Lett. 1997, 38, 1725.
5. (b) Zhu, G.; Cao, P.; Jiang, Q.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 1799.
6. (c) Zhu, G.; Chen, Z.; Jiang, Q.; Xiao, D; Cao, P.; Zhang, X. J. Am. Chem. Soc. 1997, 119, 3836.
7. See also, (d) Langer, F.; Püntener, K.; Stürmer, R.; Knochel, P.; Tetrahedron: Asymmetry 1997, 8, 715.
8. See for example Hayashi, T.; Ohno, A.; Lu, S.; Matsumoto, Y.; Fukuyo, E.; Yanagi, K. J. Am. Chem. Soc. 1994, 116, 4221, and earlier papers in the series.
9. Fujii, N.; Kakiuchi, F.; Yamada, A.; Chatani, N.; Murai, S.Chem Lett. 1997, 425.
10. Hayashi, Y.; Sakai, H.; Kaneta, N.; Uemura, M. J. Organomet. Chem. 1995, 503, 143.
11. Christian, P. W. N.; Gibson, S. E.; Gil, R.; Jones, P. C. V.; Marcos, C. F.; Prechtl, F.; Wierzchleyski, A. T. Recl. Trav. Chim. Pays-Bas 1995, 114, 195.
12. For a recent example of a phosphonate substituted system, see Müller, T. J. J. Tetrahedron Lett. 1997, 38, 1025. See also reference 5.
13. Ewin, R. A.; Price, D. A.; Simpkins, N. S.; MacLeod, A. M.; Watt, A. P. J. Chem. Soc., Perkin Trans. 1 1997, 401.
14. iPrOH-hexane as the eluant (flow rate of Iml/ min and detection at 256 nm); retention times Rt = 35 min (major enantiomer) and 43 min.
15. The absolute configuration was established by an X-ray structural determination based on the collection of low-temperature data, including Friedel equivalents, and by refinement of a Flack parameter [value 0.00(4)], see Flack, H. D. Acta Crystallogr., Sect. A 1983, 39, 876.
16. We have observed the same limitations to the chiral lithium amide metallation of a ferrocene, see Price, D.; Simpkins, N. S. Tetrahedron Lett. 1995, 36, 6135. The effect could be due to activation of the phosphine oxide through silylation on oxygen.
17. Attempted transmetallation reactions of 9 resulted in cleavage of the phosphine oxide.
18. Coumbe, T.; Lawrence, N. J.; Muhammad, F. TetrahedronLett. 1994, 35, 625.
19. +, 100%].
20. The relative configuration of 19 was established from a low temperature X-ray structure determination.
21. 2P(O)Cl, following a published procedure, see Losilkina, V. I.; Estekhina, M. N.; Baranetskaya, N. K.; Setkina, V. N. J. Organomet. Chem. 1986, 299, 187.