Phosphonites based on the paracyclophane backbone: New ligands for highly selective rhodium-catalyzed asymmetric hydrogenation

Organic Letters

Volumn 3, Issue 23, 2001, Pages 3687-3690

  Zanotti Gerosa, Antonio ^a   Malan, Christophe ^a   Herzberg, Daniela ^a  

^a Chirotech Technology Limited   (United Kingdom)

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ARTICLE;

EID: 0000870085     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0166193     Document Type: Article

References (21)

1. (a) Comprehensive Asymmetric Catalysis; Jacobsen, E. N., Pfalz, A., Yamamoto, H., Eds.; Springer: New York, 1999.
2. (b) Noyori, R. Asymmetric Catalysis in Organic Synthesis; John Wiley & Sons: New York, 1993.
3. (a) RajanBabu T. V.; Ayers, T. A.; Halliday, G. A.; You, K. K.; Calabrese, J. C. J. Org. Chem. 1997, 62, 6012.
4. (b) Selke, R.; Ohff, M.; Riepe, A. Tetrahedron 1996, 52, 15079.
5. (a) Reetz, M.; Gosberg, A.; Goddard, R.; Kyung, S. Chem. Commun. 1998, 2077.
6. (b) Reetz, M.; Gosberg, A. PCT Appl. WO 00/14096, 2000.
7. (c) Pastor, S. D.; Shum, S. P. Ciba Speciality Chemical Corporation U.S. Patent 5,817,850, 1998.
8. Reetz, M.; Neugebauer, T. Angew. Chem., Int. Ed. 1999, 38, 179,
9. Van den Berg, M.; Minnaard, A. J.; Schudde, E. P.; van Esch, J.; de Vries, A. H. M.; de Vries, J. G.; Feringa, B. L. J. Am. Chem. Soc. 2000, 122, 11539.
10. (a) Reetz, M.; Sell, T. Tetrahedron Lett. 2000, 41, 6333.
11. (b) Claver, C.; Fernandez, E.; Gillon, A.; Heslop, K.; Hyett, D. J.; Martorell, A.; Orpen, G. A.; Pringle, P. G. Chem. Commun. 2000, 961.
12. Reetz, M.; Mehler, G. Angew. Chem., Int. Ed. 2000, 39, 3889.
13. A similar concept has recently been applied to the synthesis of phosphite ligands; see ref 4.
14. Pye, P. J.; Rossen, K.; Reamer, R. A.; Tsou, N. N.; Volante, R. P.; Reider, P. J. J. Am. Chem. Soc. 1997, 119, 6207.
15. Burk, M. J.; Hems, W.; Herzberg, D.; Malan, C.; Zanotti-Gerosa, A. Org. Lett. 2000, 2, 4173.
16. Pye, P. J.; Rossen, K.; Volante, R. P. Merck & Co., PCT Appl. WO 97/47632, 1997. Pye, P. J.; Rossen, K.; Volante, R. P., Maliakal, A. J. Org. Chem. 1997, 62, 6462.
17. Pye, P. J.; Rossen, K.; Volante, R. P. Merck & Co., PCT Appl. WO 97/47632, 1997. Pye, P. J.; Rossen, K.; Volante, R. P., Maliakal, A. J. Org. Chem. 1997, 62, 6462.
18. See Supplementary Information
19. The ligands derived from 2,6-dimethylphenol, 2-naphthol, both enantiomers of TADDOL and 1,2-diphenyl-ethane-diol, were prepared and tested in rhodium-catalysed hydrogenation of dehydroamino acids. The results were inferior to the ones obtained with ligands 1a,b.
20. Reetz, M. T.; Gosberg, A. Tetrahedron: Asymmetry 1999, 2129.
21. See ref 4 for bidentate phosphites having a chiral backbone and their use in rhodium-catalyzed hydrogenation of dimethyl itaconate. The stereochemistry of the product is determined by the stereochemistry of the P/O unit.