Substituent effects in the double diastereotopic differentiation of α-diazophosphonates via intramolecular cyclopropanation

Tetrahedron Asymmetry

Volumn 14, Issue 7, 2003, Pages 873-880

  Moore, Joel D ^a   Hanson, Paul R ^a  

^a UNIVERSITY OF KANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALLYL ALCOHOL; CARBENE; ESTER DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; BIOTRANSFORMATION; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CATALYST; CHIRALITY; CYCLOPROPANATION; MOLECULAR INTERACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0037418797     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(03)00081-8     Document Type: Article

References (42)

1. Kafarski P., Lejczak B. Curr. Med. Chem.: Anti-Cancer Agents. 1:2001;301-312.
2. Quin L.D. A Guide to Organophosphorus Chemistry. 2000;Wiley-Interscience, New York.
3. Kukhar V.P., Hudson H.R. Aminophosphonic and Aminophosphinic Acids. 2000;John Wiley & Sons, Inc, New York.
4. Seto H., Kuzuyama T. Nat. Prod. Rep. 16:1999;580-596.
5. Mader M.M., Bartlett P.A. Chem. Rev. 97:1997;1281-1301.
6. Franz J.E., Mao M.K., Sikorski J.A. Glyphosate: A Unique Global Herbicide. 1997;American Chemical Society, Washington, DC.
7. Engel R. Handbook of Organo-phosphorus Chemistry. 1992;Marcel Dekker, Inc, New York.
8. Kafarski P., Lejczak B. Phosphorus, Sulfur and Silicon. 63:1991;193-215.
9. Dhawan B., Redmore D. Phosphorus and Sulfur. 32:1987;119.
10. Kukhar V.P., Svistunova N.Y., Solodenko V.A., Soloshonok V.A. Russ. Chem. Rev. 62:1993;261.
11. Natchev I.A. Bull. Chem. Soc. Jpn. 61:1988;3699-3704.
12. Kovach I.M., Mckay L., Vander Velde D. Chirality. 5:1993;143-149.
13. For reviews on the asymmetric synthesis of phosphorus compounds, including P-chiral phosphorus compounds, see: (a) Kolodiazhnyi, O. I. Tetrahedron: Asymmetry 1998, 9, 1279-1332; (b) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375-1411. For recent examples of the synthesis and use of P-chiral compounds, see: (c) Han, L.-B.; Zhao, C.-Q.; Onozawa, S.-y.; Goto, M.; Tanaka, M. J. Am. Chem. Soc. 2002, 124, 3842-3843; (d) Al-Masum, M.; Kumaraswamy, G.; Livinghouse, T. J. Org. Chem. 2000, 65, 4776-4778; (e) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T.; Su, X. J. Am. Chem. Soc. 1999, 121, 4982-4991; (f) Gilbertson, S. R.; Genov, D. G.; Rheingold, A. L. Org. Lett. 2000, 2, 2885-2888; (g) Buono, G.; Chiodi, O.; Wills, M. Synlett 1999, 377-388; (h) Denmark, S. E.; Chen, C.-T. J. Am. Chem. Soc. 1995, 117, 11879-11897.
14. For reviews on the asymmetric synthesis of phosphorus compounds, including P-chiral phosphorus compounds, see: (a) Kolodiazhnyi, O. I. Tetrahedron: Asymmetry 1998, 9, 1279-1332; (b) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375-1411. For recent examples of the synthesis and use of P-chiral compounds, see: (c) Han, L.-B.; Zhao, C.-Q.; Onozawa, S.-y.; Goto, M.; Tanaka, M. J. Am. Chem. Soc. 2002, 124, 3842-3843; (d) Al-Masum, M.; Kumaraswamy, G.; Livinghouse, T. J. Org. Chem. 2000, 65, 4776-4778; (e) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T.; Su, X. J. Am. Chem. Soc. 1999, 121, 4982-4991; (f) Gilbertson, S. R.; Genov, D. G.; Rheingold, A. L. Org. Lett. 2000, 2, 2885-2888; (g) Buono, G.; Chiodi, O.; Wills, M. Synlett 1999, 377-388; (h) Denmark, S. E.; Chen, C.-T. J. Am. Chem. Soc. 1995, 117, 11879-11897.
15. For reviews on the asymmetric synthesis of phosphorus compounds, including P-chiral phosphorus compounds, see: (a) Kolodiazhnyi, O. I. Tetrahedron: Asymmetry 1998, 9, 1279-1332; (b) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375-1411. For recent examples of the synthesis and use of P-chiral compounds, see: (c) Han, L.-B.; Zhao, C.-Q.; Onozawa, S.-y.; Goto, M.; Tanaka, M. J. Am. Chem. Soc. 2002, 124, 3842-3843; (d) Al-Masum, M.; Kumaraswamy, G.; Livinghouse, T. J. Org. Chem. 2000, 65, 4776-4778; (e) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T.; Su, X. J. Am. Chem. Soc. 1999, 121, 4982-4991; (f) Gilbertson, S. R.; Genov, D. G.; Rheingold, A. L. Org. Lett. 2000, 2, 2885-2888; (g) Buono, G.; Chiodi, O.; Wills, M. Synlett 1999, 377-388; (h) Denmark, S. E.; Chen, C.-T. J. Am. Chem. Soc. 1995, 117, 11879-11897.
16. For reviews on the asymmetric synthesis of phosphorus compounds, including P-chiral phosphorus compounds, see: (a) Kolodiazhnyi, O. I. Tetrahedron: Asymmetry 1998, 9, 1279-1332; (b) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375-1411. For recent examples of the synthesis and use of P-chiral compounds, see: (c) Han, L.-B.; Zhao, C.-Q.; Onozawa, S.-y.; Goto, M.; Tanaka, M. J. Am. Chem. Soc. 2002, 124, 3842-3843; (d) Al-Masum, M.; Kumaraswamy, G.; Livinghouse, T. J. Org. Chem. 2000, 65, 4776-4778; (e) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T.; Su, X. J. Am. Chem. Soc. 1999, 121, 4982-4991; (f) Gilbertson, S. R.; Genov, D. G.; Rheingold, A. L. Org. Lett. 2000, 2, 2885-2888; (g) Buono, G.; Chiodi, O.; Wills, M. Synlett 1999, 377-388; (h) Denmark, S. E.; Chen, C.-T. J. Am. Chem. Soc. 1995, 117, 11879-11897.
17. For reviews on the asymmetric synthesis of phosphorus compounds, including P-chiral phosphorus compounds, see: (a) Kolodiazhnyi, O. I. Tetrahedron: Asymmetry 1998, 9, 1279-1332; (b) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375-1411. For recent examples of the synthesis and use of P-chiral compounds, see: (c) Han, L.-B.; Zhao, C.-Q.; Onozawa, S.-y.; Goto, M.; Tanaka, M. J. Am. Chem. Soc. 2002, 124, 3842-3843; (d) Al-Masum, M.; Kumaraswamy, G.; Livinghouse, T. J. Org. Chem. 2000, 65, 4776-4778; (e) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T.; Su, X. J. Am. Chem. Soc. 1999, 121, 4982-4991; (f) Gilbertson, S. R.; Genov, D. G.; Rheingold, A. L. Org. Lett. 2000, 2, 2885-2888; (g) Buono, G.; Chiodi, O.; Wills, M. Synlett 1999, 377-388; (h) Denmark, S. E.; Chen, C.-T. J. Am. Chem. Soc. 1995, 117, 11879-11897.
18. For reviews on the asymmetric synthesis of phosphorus compounds, including P-chiral phosphorus compounds, see: (a) Kolodiazhnyi, O. I. Tetrahedron: Asymmetry 1998, 9, 1279-1332; (b) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375-1411. For recent examples of the synthesis and use of P-chiral compounds, see: (c) Han, L.-B.; Zhao, C.-Q.; Onozawa, S.-y.; Goto, M.; Tanaka, M. J. Am. Chem. Soc. 2002, 124, 3842-3843; (d) Al-Masum, M.; Kumaraswamy, G.; Livinghouse, T. J. Org. Chem. 2000, 65, 4776-4778; (e) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T.; Su, X. J. Am. Chem. Soc. 1999, 121, 4982-4991; (f) Gilbertson, S. R.; Genov, D. G.; Rheingold, A. L. Org. Lett. 2000, 2, 2885-2888; (g) Buono, G.; Chiodi, O.; Wills, M. Synlett 1999, 377-388; (h) Denmark, S. E.; Chen, C.-T. J. Am. Chem. Soc. 1995, 117, 11879-11897.
19. For reviews on the asymmetric synthesis of phosphorus compounds, including P-chiral phosphorus compounds, see: (a) Kolodiazhnyi, O. I. Tetrahedron: Asymmetry 1998, 9, 1279-1332; (b) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375-1411. For recent examples of the synthesis and use of P-chiral compounds, see: (c) Han, L.-B.; Zhao, C.-Q.; Onozawa, S.-y.; Goto, M.; Tanaka, M. J. Am. Chem. Soc. 2002, 124, 3842-3843; (d) Al-Masum, M.; Kumaraswamy, G.; Livinghouse, T. J. Org. Chem. 2000, 65, 4776-4778; (e) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T.; Su, X. J. Am. Chem. Soc. 1999, 121, 4982-4991; (f) Gilbertson, S. R.; Genov, D. G.; Rheingold, A. L. Org. Lett. 2000, 2, 2885-2888; (g) Buono, G.; Chiodi, O.; Wills, M. Synlett 1999, 377-388; (h) Denmark, S. E.; Chen, C.-T. J. Am. Chem. Soc. 1995, 117, 11879-11897.
20. For reviews on the asymmetric synthesis of phosphorus compounds, including P-chiral phosphorus compounds, see: (a) Kolodiazhnyi, O. I. Tetrahedron: Asymmetry 1998, 9, 1279-1332; (b) Pietrusiewicz, K. M.; Zablocka, M. Chem. Rev. 1994, 94, 1375-1411. For recent examples of the synthesis and use of P-chiral compounds, see: (c) Han, L.-B.; Zhao, C.-Q.; Onozawa, S.-y.; Goto, M.; Tanaka, M. J. Am. Chem. Soc. 2002, 124, 3842-3843; (d) Al-Masum, M.; Kumaraswamy, G.; Livinghouse, T. J. Org. Chem. 2000, 65, 4776-4778; (e) Denmark, S. E.; Stavenger, R. A.; Wong, K.-T.; Su, X. J. Am. Chem. Soc. 1999, 121, 4982-4991; (f) Gilbertson, S. R.; Genov, D. G.; Rheingold, A. L. Org. Lett. 2000, 2, 2885-2888; (g) Buono, G.; Chiodi, O.; Wills, M. Synlett 1999, 377-388; (h) Denmark, S. E.; Chen, C.-T. J. Am. Chem. Soc. 1995, 117, 11879-11897.
21. (a) Stoianova, D. S.; Hanson, P. R. Org. Lett. 2000, 2, 1769-1772;
22. (b) Moore, J. D.; Sprott, K. T.; Wrobleski, A. D.; Hanson, P. R. Org. Lett. 2002, 4, 2357-2360.
23. For examples of double diastereoselective processes, see: (c) Kurth, M. J.; Brown, E. G. J. Am. Chem. Soc. 1987, 109, 6844-6845;
24. (d) McKew, J. C.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 1994, 59, 3389;
25. (e) Martin, S. F.; Spaller, M. R.; Liras, S.; Hartmann, B. J. Am. Chem. Soc. 1994, 116, 4493-4494.
26. Doyle M.P., McKervey M.A., Ye T. Modern Catalytic Methods for Organic Synthesis with Diazo Compounds. 1998;John Wiley & Sons, Inc, New York.
27. Doyle M.P., Forbes D.C. Chem. Rev. 98:1998;911-936. and references cited therein.
28. Davies H.M.L., Huby N.J.S., Cantrell W.R. Jr., Olive J.L. J. Am. Chem. Soc. 115:1993;9468-9479.
29. Davies H.M.L., Cantrell W.R. Tetrahedron Lett. 32:1991;6509-6512.
30. Moore J.D., Sprott K.T., Hanson P.R. J. Org. Chem. 67:2002;8123-8129.
31. Davies H.M.L., Doan B.D. J. Org. Chem. 64:1999;8501-8508.
32. 2-symmetric compounds, see: (a) Magnuson, S. R. Tetrahedron 1995, 51, 2167-2213; (b) Schreiber, S. L.; Poss, C. S. Acc. Chem. Res. 1994, 27, 9-17. See also: (c) Hoye, T. R.; Peck, D. R.; Trumper, P. K. J. Am. Chem. Soc. 1981, 103, 5618; (d) Hoye, T. R.; Peck, D. R.; Swanson, T. A. J. Am. Chem. Soc. 1984, 106, 2738; (e) Schreiber, S. L.; Wang, Z. J. Am. Chem. Soc. 1985, 107, 5303; (f) Ward, D. Chem. Soc. Rev. 1990, 19, 1-19; (g) Shepherd, J. N.; Na, J.; Myles, D. C. J. Org. Chem. 1997, 62, 4558-4559.
33. 2-symmetric compounds, see: (a) Magnuson, S. R. Tetrahedron 1995, 51, 2167-2213; (b) Schreiber, S. L.; Poss, C. S. Acc. Chem. Res. 1994, 27, 9-17. See also: (c) Hoye, T. R.; Peck, D. R.; Trumper, P. K. J. Am. Chem. Soc. 1981, 103, 5618; (d) Hoye, T. R.; Peck, D. R.; Swanson, T. A. J. Am. Chem. Soc. 1984, 106, 2738; (e) Schreiber, S. L.; Wang, Z. J. Am. Chem. Soc. 1985, 107, 5303; (f) Ward, D. Chem. Soc. Rev. 1990, 19, 1-19; (g) Shepherd, J. N.; Na, J.; Myles, D. C. J. Org. Chem. 1997, 62, 4558-4559.
34. 2-symmetric compounds, see: (a) Magnuson, S. R. Tetrahedron 1995, 51, 2167-2213; (b) Schreiber, S. L.; Poss, C. S. Acc. Chem. Res. 1994, 27, 9-17. See also: (c) Hoye, T. R.; Peck, D. R.; Trumper, P. K. J. Am. Chem. Soc. 1981, 103, 5618; (d) Hoye, T. R.; Peck, D. R.; Swanson, T. A. J. Am. Chem. Soc. 1984, 106, 2738; (e) Schreiber, S. L.; Wang, Z. J. Am. Chem. Soc. 1985, 107, 5303; (f) Ward, D. Chem. Soc. Rev. 1990, 19, 1-19; (g) Shepherd, J. N.; Na, J.; Myles, D. C. J. Org. Chem. 1997, 62, 4558-4559.
35. 2-symmetric compounds, see: (a) Magnuson, S. R. Tetrahedron 1995, 51, 2167-2213; (b) Schreiber, S. L.; Poss, C. S. Acc. Chem. Res. 1994, 27, 9-17. See also: (c) Hoye, T. R.; Peck, D. R.; Trumper, P. K. J. Am. Chem. Soc. 1981, 103, 5618; (d) Hoye, T. R.; Peck, D. R.; Swanson, T. A. J. Am. Chem. Soc. 1984, 106, 2738; (e) Schreiber, S. L.; Wang, Z. J. Am. Chem. Soc. 1985, 107, 5303; (f) Ward, D. Chem. Soc. Rev. 1990, 19, 1-19; (g) Shepherd, J. N.; Na, J.; Myles, D. C. J. Org. Chem. 1997, 62, 4558-4559.
36. 2-symmetric compounds, see: (a) Magnuson, S. R. Tetrahedron 1995, 51, 2167-2213; (b) Schreiber, S. L.; Poss, C. S. Acc. Chem. Res. 1994, 27, 9-17. See also: (c) Hoye, T. R.; Peck, D. R.; Trumper, P. K. J. Am. Chem. Soc. 1981, 103, 5618; (d) Hoye, T. R.; Peck, D. R.; Swanson, T. A. J. Am. Chem. Soc. 1984, 106, 2738; (e) Schreiber, S. L.; Wang, Z. J. Am. Chem. Soc. 1985, 107, 5303; (f) Ward, D. Chem. Soc. Rev. 1990, 19, 1-19; (g) Shepherd, J. N.; Na, J.; Myles, D. C. J. Org. Chem. 1997, 62, 4558-4559.
37. 2-symmetric compounds, see: (a) Magnuson, S. R. Tetrahedron 1995, 51, 2167-2213; (b) Schreiber, S. L.; Poss, C. S. Acc. Chem. Res. 1994, 27, 9-17. See also: (c) Hoye, T. R.; Peck, D. R.; Trumper, P. K. J. Am. Chem. Soc. 1981, 103, 5618; (d) Hoye, T. R.; Peck, D. R.; Swanson, T. A. J. Am. Chem. Soc. 1984, 106, 2738; (e) Schreiber, S. L.; Wang, Z. J. Am. Chem. Soc. 1985, 107, 5303; (f) Ward, D. Chem. Soc. Rev. 1990, 19, 1-19; (g) Shepherd, J. N.; Na, J.; Myles, D. C. J. Org. Chem. 1997, 62, 4558-4559.
38. 2-symmetric compounds, see: (a) Magnuson, S. R. Tetrahedron 1995, 51, 2167-2213; (b) Schreiber, S. L.; Poss, C. S. Acc. Chem. Res. 1994, 27, 9-17. See also: (c) Hoye, T. R.; Peck, D. R.; Trumper, P. K. J. Am. Chem. Soc. 1981, 103, 5618; (d) Hoye, T. R.; Peck, D. R.; Swanson, T. A. J. Am. Chem. Soc. 1984, 106, 2738; (e) Schreiber, S. L.; Wang, Z. J. Am. Chem. Soc. 1985, 107, 5303; (f) Ward, D. Chem. Soc. Rev. 1990, 19, 1-19; (g) Shepherd, J. N.; Na, J.; Myles, D. C. J. Org. Chem. 1997, 62, 4558-4559.
39. 11 was prepared from addition of trimethylsulfonium ylide to (S)-benzyl-glycidyl ether, see: Davoille, R. J.; Rutherford, D. T.; Christie, S. D. R. Tetrahedron Lett. 2000, 41, 1255-1259.
40. S.
41. 1H chemical shift of the protons on the bicyclic system which are endo to the P=O group are further downfield than their exo counterparts.
42. R) also substantially increased to a ratio of 7.4:1 (from 3.6:1 for the allyl-based system 1).