Enantioselective synthesis of cyclopropylphosphonates containing quaternary stereocenters using a D2-symmetric chiral catalyst Rh 2(S-biTISP)2

Organic Letters

Volumn 6, Issue 13, 2004, Pages 2117-2120

  Davies, Huw M L ^a   Lee, Gene H ^a  

^a UNIVERSITY AT BUFFALO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; PHOSPHONIC ACID DERIVATIVE; RHODIUM; STYRENE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; CYCLOPROPANATION; DIASTEREOISOMER; ENANTIOSELECTIVITY; REACTION ANALYSIS; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 3142760938     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049525c     Document Type: Article

References (42)

1. (a) Erion, M. D.; Walsh, C. T. Biochemistry 1987, 26, 3417.
2. (b) Groth, U.; Lehmann, L.; Richter, L.; Schöllkopf, U. Liebigs Ann. Chem. 1993, 427.
3. Hercouet, A.; Le Corre, M.; Carboni, B. Tetrahedron Lett. 2000, 41, 197.
4. Hah, J. H.; Gil, J. M.; Oh, D. Y. Tetrahedron Lett. 1999, 40, 8235.
5. Diel, P. J.; Maier, L. Phosphorus Sulfur 1984, 20, 313.
6. Reid, J. R.; Marmor, R. S. J. Org. Chem. 1978, 43, 999.
7. Duquenne, C.; Goumain, S.; Jubault, P.; Feasson, C.; Quirion, J.-C. Org. Lett. 2000, 2, 453.
8. Hanessian, S.; Cantin, L.-D.; Roy, S.; Andretti, D.; Gomtsyan, A. Tetrahedron Lett. 1997, 38, 1103.
9. Hirao, T.; Hagihara, M.; Agawa, T. Bull. Chem. Soc. Jpn. 1985, 58, 3104.
10. (a) Minami, T.; Yamanouchi, T.; Tokumasu, S.; Hirao, I. Bull. Chem. Soc. Jpn. 1984, 57, 2127.
11. (b) Midura, W. H.; Krysiak, J. A.; Wieczorek, M. W.; Majzner, W. R.; Mikolajczk, M. Chem. Commun. 1998, 1109.
12. (c) Midura, W. H.; Krysiak, J. A.; Mikolajczk, M. Tetrahedron 1999, 55, 14791.
13. (d) Yamazaki, S.; Takada, T.; Imanishi, T.; Moriguchi, Y.; Yamabe, S. J. Org. Chem. 1998, 63, 5919.
14. (a) Jubault, P.; Goumain, S.; Feasson, C.; Collignon, N. Tetrahedron 1998, 54, 14767.
15. (b) Jubault, P.; Goumain, S.; Feasson, C.; Collignon, N. Synthesis 1999, 1903.
16. (c) Jubault, P.; Goumain, S.; Feasson, C.; Collignon, N. Tetrahedron Lett. 1999, 40, 8099.
17. (a) Fadel, A.; Tesson, N. Eur. J. Org. Chem. 2000, 2153.
18. (b) Fadel, A.; Tesson, N. Tetrahedron: Asymmetry 2000, 11, 2023.
19. Griffin, C. E.; Kraas, E.; Terasawa, H.; Griffin, G. W.; Lankin, D. C. J. Heterocycl. Chem. 1978, 15, 523.
20. (a) Nasser, J.; About-Jaudet, E.; Collignon, N. Phosphorus, Sulfur Silicon 1990, 54, 111.
21. (b) Diel, P. J.; Maier, L. Phosphorus Sulfur 1984, 20, 313.
22. Kondo, K.; Liu, Y.; Tunemoto, D. J. Chem. Soc., Perkin Trans, 1 1974, 1279.
23. Davies, H. M. L.; Antoulinakis, E. G. Org. React. 2001, 57, 1.
24. (a) Seyferth, D.; Marmor, R. S.; Hubert, P. J. Org. Chem. 1971, 36, 1379.
25. (b) Regitz, M.; Scherer, H.; Anschütz, W. Tetrahedron Lett. 1970, 10, 753.
26. (c) Hanson, P. R.; Sprott, K. T.; Wrobleski, A. D. Tetrahedron Lett. 1999, 40, 1455.
27. (d) Hanson, P. R.; Moore, J. D.; Sprott, K. T. J. Org. Chem. 2002, 67, 8123.
28. (e) Hanson, P. R.; Moore, J. D. Tetrahedron: Asymmetry 2003, 14, 873.
29. (f) Hanson, P. R.; Moore, J. D.; Sprott, K. T.; Wrobleski, A. D. Org. Lett. 2002, 4, 2357.
30. (g) Simonneaux, G.; Montigny, F. D.; Roth, P. C.; Gulea, M.; Masson, S. Tetrahedron Lett. 2002, 43, 3685.
31. (h) Lewis, R. T.; Motherwell, W. B. Tetrahedron Lett. 1988, 29, 5033.
32. (i) Zaragoza, F. Tetrahedron 1997, 53, 3425.
33. (j) Paul-Roth, C.; Montigny, F. D.; Rethore, G.; Simonneaux, G.; Gulea, M.; Masson, S. J. Mol. Cat. 2003, 201, 79.
34. Davies, H. M. L.; Beckwith, R. E. J. Chem. Rev. 2003, 103, 2861.
35. Davies, H. M. L.; Hodges, L. M.; Matasi, J. J.; Hansen, T.; Stafford, D. G. Tetrahedron Lett. 1998, 39, 4417.
36. Davies, H. M. L. Eur. J. Org. Chem. 1999, 2459, 9.
37. Davies, H. M. L.; Townsend, R. J. J. Org. Chem. 2001, 66, 6595.
38. Davies, H. M. L.; Bruzinski, P.; Hutcheson, D. K.; Kong, N.; Fall, M. J. J. Am. Chem. Soc. 1996, 118, 6897.
39. See Supporting Information for the synthesis of the diazomethylphosphonates.
40. X-ray crystallographic data have been submitted to the Cambridge Structural Database [Gerlits, O. O.; Coppens, P. Private communication].
41. Davies, H. M. L.; Panaro, S. A. Tetrahedron Lett. 1999, 40, 5287.
42. Davies, H. M. L. In Advances in Cycloaddition; Haramata, M. E., Eds.; JAI Press: Greenwich, CT, 1999; Vol. 5, pp 119-164.