Enantioselective synthesis of α-hydroxy and α-amino phosphonates via catalytic asymmetric hydrogenation

Organic Letters

Volumn 1, Issue 3, 1999, Pages 387-390

  Burk, Mark J ^a,b   Stammers, Timothy A ^a,c   Straub, Judith A ^a,d  

^a DUKE UNIVERSITY   (United States)

^b Chirotech Ltd   (United Kingdom)

^c UNIVERSITY OF TORONTO   (Canada)

^d PHARMACOPEIA INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000634228     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9906099     Document Type: Article

References (29)

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11. (e) Burk, M. J.; Allen, J. G.; Keisman, W. F. J. Am. Chem. Soc. 1998, 120, 657.
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15. Examples of the catalytic asymmetric hydrogenation of enamido phosphonates include: (a) Schmidt, U.; Oehme, G.; Krause, H. Synth. Commun. 1996, 26, 777.
16. (b) Talley, J. J. US 5,321,153 14.6.94; Appl. 898,253 15.6.92.
17. (c) Schollkopf, U.; Hoppe, I.; Thiele, A. Liebigs Ann. Chem. 1985, 555. Analogous enamido phosphinic acid esters: Dwars, T.; Schmidt, U.; Fischer, C.; Grassert, I.; Kempe, R.; Frohlich, R.; Drauz, K, Oehme, G. Angew. Chem., Int. Ed. Engl. 1998, 37, 2851.
18. (c) Schollkopf, U.; Hoppe, I.; Thiele, A. Liebigs Ann. Chem. 1985, 555. Analogous enamido phosphinic acid esters: Dwars, T.; Schmidt, U.; Fischer, C.; Grassert, I.; Kempe, R.; Frohlich, R.; Drauz, K, Oehme, G. Angew. Chem., Int. Ed. Engl. 1998, 37, 2851.
19. Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1995, 60, 6656.
20. α-Keto phosphonate intermediates of 3a-h proved to be unstable, decomposing over several days at room temperature.
21. 31P NMR in stereochemical Ananlysis; Verkade, J. G., Quin, L. D., Eds.; VCH Publishers Inc.: Deerfield Beach, FL, 1987; p 379). (formula presented)
22. Enantiomeric excess determined by comparison to racemate. Race-mates for 4a, 8, and 9 were prepared by hydrogenation of the precusor olefins with the [(DiPFc)Rh(COD)]OTf catalyts (DiPFc = 1,1′-bis-(diisopropylphosphino)ferrocenyl). Racemic mixtures for 4b-h were prepared throuah the hydrogenation of the precursor olefins with 10% Pd/ C.
23. Halpern, J. In Asymmetric Catalysis; Morrison, J. D., Ed.; Academic Press: New York, 1985; Vol. 5, p 41.
24. (b) Sawamura, M.; Kuwano, R.; Ito, Y. J. Am. Chem. Soc. 1995, 117, 9602.
25. (c) Ojima, I.; Kogure, T.; Yoda, N. J. Org. Chem. 1980, 45, 4728.
26. Burk, M. J.; Bienewald, S.; Challenger, S.; Derrick, A.; Ramsden, J. A. J. Org. Chem. 1999, 64, 3290.
27. Zon, J. Synthesis 1981, 324.
28. (a) Burk, M. J.; Bienewald, F.; Harris, M.; Zanotti-Gerosa, A. Angew. Chem., Int. Ed. Engl. 1998, 37, 1931.
29. (b) Burk, M. J.; Casy, G.; Johnson, N. J. Org. Chem. 1998, 63, 6084.