The catalytic asymmetric aminohydroxylation of unsaturated phosphonates

Journal of Organic Chemistry

Volumn 64, Issue 22, 1999, Pages 8379-8385

  Thomas, Allen A ^a   Sharpless, K Barry ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; CINCHONA ALKALOID; OSMIUM; PHOSPHATASE; PHOSPHONIC ACID DERIVATIVE; TOLUENESULFONAMIDE DERIVATIVE; URETHAN;

AMINATION; ARTICLE; CATALYSIS; CATALYST; CRYSTALLIZATION; DRUG HYDROLYSIS; ENANTIOMER; HYDROXYLATION; OPTICAL ROTATION; RACEMIC MIXTURE; STEREOCHEMISTRY; THIN LAYER CHROMATOGRAPHY;

EID: 0033615596     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990060r     Document Type: Article

References (45)

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2. (1)(a) Dellaria, J. F., Jr.; Maki, R. G.; Stein, H. H.; Cohen, J.; Whittern, D.; Marsh, K.; Hoffman, D. J.; Plattner, J. J.; Perun, T. J. J. Med. Chem. 1990, 33, 534. (b) Wester, R. T.; Chambers, R. J.; Green, M. D.; Murphy, W. R. Bioorg. Med. Chem. Lett. 1994, 4, 2005. For reviews on phosphonates, see: Kafarski, P.; Lejczak, B. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 63, 193. Dhawan, B.; Redmore, D. Phosphorus Sulfur 1987, 32, 119.
3. (1)(a) Dellaria, J. F., Jr.; Maki, R. G.; Stein, H. H.; Cohen, J.; Whittern, D.; Marsh, K.; Hoffman, D. J.; Plattner, J. J.; Perun, T. J. J. Med. Chem. 1990, 33, 534. (b) Wester, R. T.; Chambers, R. J.; Green, M. D.; Murphy, W. R. Bioorg. Med. Chem. Lett. 1994, 4, 2005. For reviews on phosphonates, see: Kafarski, P.; Lejczak, B. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 63, 193. Dhawan, B.; Redmore, D. Phosphorus Sulfur 1987, 32, 119.
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8. (a) Smith, A. B., III.; Yager, K. M.; Taylor, C. M. J. Am. Chem. Soc. 1905, 117, 10879. (b) Hanessian, S.; Bennani, Y. L. Tetrahedron Lett. 1990, 31, 6465. Hanessian, S.; Bennani, Y. L. Synthesis 1994, 1272. Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1996, 60, 6656. (e) Maury, C.; Gharbaoui, T.; Royer, J.; Husson, H.-P. J. Org. Chem. 1996, 61, 3687. (f) Demir, A. S.; Tanyeli, C.; Sesenoglu, O.; Demic, S. Tetrahedron Lett. 1996, 37, 407. (g) Meier, C.; Laux, W. H. G. Tetrahedron 1996, 52, 589. (h) Schmidt, U.; Oehme, G.; Krause, H. Synth. Commun. 1996, 26, 777. Ferris, L.; Haigh, D.; Moody, C. J. Synlett 1995, 921. (j) Tao, M.; Bihovsky, R.; Wells, G. J.; Mallamo, J. P. J. Med. Chem. 1998, 41, 3912.
9. (a) Smith, A. B., III.; Yager, K. M.; Taylor, C. M. J. Am. Chem. Soc. 1905, 117, 10879. (b) Hanessian, S.; Bennani, Y. L. Tetrahedron Lett. 1990, 31, 6465. Hanessian, S.; Bennani, Y. L. Synthesis 1994, 1272. Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1996, 60, 6656. (e) Maury, C.; Gharbaoui, T.; Royer, J.; Husson, H.-P. J. Org. Chem. 1996, 61, 3687. (f) Demir, A. S.; Tanyeli, C.; Sesenoglu, O.; Demic, S. Tetrahedron Lett. 1996, 37, 407. (g) Meier, C.; Laux, W. H. G. Tetrahedron 1996, 52, 589. (h) Schmidt, U.; Oehme, G.; Krause, H. Synth. Commun. 1996, 26, 777. Ferris, L.; Haigh, D.; Moody, C. J. Synlett 1995, 921. (j) Tao, M.; Bihovsky, R.; Wells, G. J.; Mallamo, J. P. J. Med. Chem. 1998, 41, 3912.
10. (a) Smith, A. B., III.; Yager, K. M.; Taylor, C. M. J. Am. Chem. Soc. 1905, 117, 10879. (b) Hanessian, S.; Bennani, Y. L. Tetrahedron Lett. 1990, 31, 6465. Hanessian, S.; Bennani, Y. L. Synthesis 1994, 1272. Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1996, 60, 6656. (e) Maury, C.; Gharbaoui, T.; Royer, J.; Husson, H.-P. J. Org. Chem. 1996, 61, 3687. (f) Demir, A. S.; Tanyeli, C.; Sesenoglu, O.; Demic, S. Tetrahedron Lett. 1996, 37, 407. (g) Meier, C.; Laux, W. H. G. Tetrahedron 1996, 52, 589. (h) Schmidt, U.; Oehme, G.; Krause, H. Synth. Commun. 1996, 26, 777. Ferris, L.; Haigh, D.; Moody, C. J. Synlett 1995, 921. (j) Tao, M.; Bihovsky, R.; Wells, G. J.; Mallamo, J. P. J. Med. Chem. 1998, 41, 3912.
11. (a) Smith, A. B., III.; Yager, K. M.; Taylor, C. M. J. Am. Chem. Soc. 1905, 117, 10879. (b) Hanessian, S.; Bennani, Y. L. Tetrahedron Lett. 1990, 31, 6465. Hanessian, S.; Bennani, Y. L. Synthesis 1994, 1272. Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1996, 60, 6656. (e) Maury, C.; Gharbaoui, T.; Royer, J.; Husson, H.-P. J. Org. Chem. 1996, 61, 3687. (f) Demir, A. S.; Tanyeli, C.; Sesenoglu, O.; Demic, S. Tetrahedron Lett. 1996, 37, 407. (g) Meier, C.; Laux, W. H. G. Tetrahedron 1996, 52, 589. (h) Schmidt, U.; Oehme, G.; Krause, H. Synth. Commun. 1996, 26, 777. Ferris, L.; Haigh, D.; Moody, C. J. Synlett 1995, 921. (j) Tao, M.; Bihovsky, R.; Wells, G. J.; Mallamo, J. P. J. Med. Chem. 1998, 41, 3912.
12. (a) Smith, A. B., III.; Yager, K. M.; Taylor, C. M. J. Am. Chem. Soc. 1905, 117, 10879. (b) Hanessian, S.; Bennani, Y. L. Tetrahedron Lett. 1990, 31, 6465. Hanessian, S.; Bennani, Y. L. Synthesis 1994, 1272. Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1996, 60, 6656. (e) Maury, C.; Gharbaoui, T.; Royer, J.; Husson, H.-P. J. Org. Chem. 1996, 61, 3687. (f) Demir, A. S.; Tanyeli, C.; Sesenoglu, O.; Demic, S. Tetrahedron Lett. 1996, 37, 407. (g) Meier, C.; Laux, W. H. G. Tetrahedron 1996, 52, 589. (h) Schmidt, U.; Oehme, G.; Krause, H. Synth. Commun. 1996, 26, 777. Ferris, L.; Haigh, D.; Moody, C. J. Synlett 1995, 921. (j) Tao, M.; Bihovsky, R.; Wells, G. J.; Mallamo, J. P. J. Med. Chem. 1998, 41, 3912.
13. (a) Smith, A. B., III.; Yager, K. M.; Taylor, C. M. J. Am. Chem. Soc. 1905, 117, 10879. (b) Hanessian, S.; Bennani, Y. L. Tetrahedron Lett. 1990, 31, 6465. Hanessian, S.; Bennani, Y. L. Synthesis 1994, 1272. Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1996, 60, 6656. (e) Maury, C.; Gharbaoui, T.; Royer, J.; Husson, H.-P. J. Org. Chem. 1996, 61, 3687. (f) Demir, A. S.; Tanyeli, C.; Sesenoglu, O.; Demic, S. Tetrahedron Lett. 1996, 37, 407. (g) Meier, C.; Laux, W. H. G. Tetrahedron 1996, 52, 589. (h) Schmidt, U.; Oehme, G.; Krause, H. Synth. Commun. 1996, 26, 777. Ferris, L.; Haigh, D.; Moody, C. J. Synlett 1995, 921. (j) Tao, M.; Bihovsky, R.; Wells, G. J.; Mallamo, J. P. J. Med. Chem. 1998, 41, 3912.
14. (a) Smith, A. B., III.; Yager, K. M.; Taylor, C. M. J. Am. Chem. Soc. 1905, 117, 10879. (b) Hanessian, S.; Bennani, Y. L. Tetrahedron Lett. 1990, 31, 6465. Hanessian, S.; Bennani, Y. L. Synthesis 1994, 1272. Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1996, 60, 6656. (e) Maury, C.; Gharbaoui, T.; Royer, J.; Husson, H.-P. J. Org. Chem. 1996, 61, 3687. (f) Demir, A. S.; Tanyeli, C.; Sesenoglu, O.; Demic, S. Tetrahedron Lett. 1996, 37, 407. (g) Meier, C.; Laux, W. H. G. Tetrahedron 1996, 52, 589. (h) Schmidt, U.; Oehme, G.; Krause, H. Synth. Commun. 1996, 26, 777. Ferris, L.; Haigh, D.; Moody, C. J. Synlett 1995, 921. (j) Tao, M.; Bihovsky, R.; Wells, G. J.; Mallamo, J. P. J. Med. Chem. 1998, 41, 3912.
15. (a) Smith, A. B., III.; Yager, K. M.; Taylor, C. M. J. Am. Chem. Soc. 1905, 117, 10879. (b) Hanessian, S.; Bennani, Y. L. Tetrahedron Lett. 1990, 31, 6465. Hanessian, S.; Bennani, Y. L. Synthesis 1994, 1272. Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1996, 60, 6656. (e) Maury, C.; Gharbaoui, T.; Royer, J.; Husson, H.-P. J. Org. Chem. 1996, 61, 3687. (f) Demir, A. S.; Tanyeli, C.; Sesenoglu, O.; Demic, S. Tetrahedron Lett. 1996, 37, 407. (g) Meier, C.; Laux, W. H. G. Tetrahedron 1996, 52, 589. (h) Schmidt, U.; Oehme, G.; Krause, H. Synth. Commun. 1996, 26, 777. Ferris, L.; Haigh, D.; Moody, C. J. Synlett 1995, 921. (j) Tao, M.; Bihovsky, R.; Wells, G. J.; Mallamo, J. P. J. Med. Chem. 1998, 41, 3912.
16. (a) Smith, A. B., III.; Yager, K. M.; Taylor, C. M. J. Am. Chem. Soc. 1905, 117, 10879. (b) Hanessian, S.; Bennani, Y. L. Tetrahedron Lett. 1990, 31, 6465. Hanessian, S.; Bennani, Y. L. Synthesis 1994, 1272. Sasai, H.; Arai, S.; Tahara, Y.; Shibasaki, M. J. Org. Chem. 1996, 60, 6656. (e) Maury, C.; Gharbaoui, T.; Royer, J.; Husson, H.-P. J. Org. Chem. 1996, 61, 3687. (f) Demir, A. S.; Tanyeli, C.; Sesenoglu, O.; Demic, S. Tetrahedron Lett. 1996, 37, 407. (g) Meier, C.; Laux, W. H. G. Tetrahedron 1996, 52, 589. (h) Schmidt, U.; Oehme, G.; Krause, H. Synth. Commun. 1996, 26, 777. Ferris, L.; Haigh, D.; Moody, C. J. Synlett 1995, 921. (j) Tao, M.; Bihovsky, R.; Wells, G. J.; Mallamo, J. P. J. Med. Chem. 1998, 41, 3912.
17. (5)(a) Yokomatsu, T.; Yoshida, Y.; Suemune, K.; Yamagishi, T.; Shibuya, S. Tetrahedron: Asymmetry 1995, 6, 365. (b) Yokomatsu, T.; Suemune, K.; Yamagishi, T.; Shibuya, S. Synlett 1995, 847. (c) Kitamura, M.; Tokunaga, M.; Pham, T.; Lubell, W. D.; Noyori, R. Tetrahedron Lett. 1995, 36, 5769. Zygmunt, J.; Gancarz, R.; Lejczak, B.; Wieczorek, P.; Kafarski, P. Bioorg. Med. Chem. Lett. 1996, 6, 2989. (e) Bongini, A.; Camerini, R.; Hofman, S.; Panunzio, M. Tetrahedron Lett. 1994, 35, 8045. (f) Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E.; Free, C. A.; Rogers, W. L.; Smith, S. A.; DeForrest, J. M.; Oehl, R. S.; Petrillo, E. W., Jr. J. Med. Chem. 1995, 38, 4557. (g) Wroblewski, A. E.; Piotrowska, D. G. Tetrahedron 1998, 54, 8123.
18. (5)(a) Yokomatsu, T.; Yoshida, Y.; Suemune, K.; Yamagishi, T.; Shibuya, S. Tetrahedron: Asymmetry 1995, 6, 365. (b) Yokomatsu, T.; Suemune, K.; Yamagishi, T.; Shibuya, S. Synlett 1995, 847. (c) Kitamura, M.; Tokunaga, M.; Pham, T.; Lubell, W. D.; Noyori, R. Tetrahedron Lett. 1995, 36, 5769. Zygmunt, J.; Gancarz, R.; Lejczak, B.; Wieczorek, P.; Kafarski, P. Bioorg. Med. Chem. Lett. 1996, 6, 2989. (e) Bongini, A.; Camerini, R.; Hofman, S.; Panunzio, M. Tetrahedron Lett. 1994, 35, 8045. (f) Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E.; Free, C. A.; Rogers, W. L.; Smith, S. A.; DeForrest, J. M.; Oehl, R. S.; Petrillo, E. W., Jr. J. Med. Chem. 1995, 38, 4557. (g) Wroblewski, A. E.; Piotrowska, D. G. Tetrahedron 1998, 54, 8123.
19. (5)(a) Yokomatsu, T.; Yoshida, Y.; Suemune, K.; Yamagishi, T.; Shibuya, S. Tetrahedron: Asymmetry 1995, 6, 365. (b) Yokomatsu, T.; Suemune, K.; Yamagishi, T.; Shibuya, S. Synlett 1995, 847. Kitamura, M.; Tokunaga, M.; Pham, T.; Lubell, W. D.; Noyori, R. Tetrahedron Lett. 1995, 36, 5769. Zygmunt, J.; Gancarz, R.; Lejczak, B.; Wieczorek, P.; Kafarski, P. Bioorg. Med. Chem. Lett. 1996, 6, 2989. (e) Bongini, A.; Camerini, R.; Hofman, S.; Panunzio, M. Tetrahedron Lett. 1994, 35, 8045. (f) Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E.; Free, C. A.; Rogers, W. L.; Smith, S. A.; DeForrest, J. M.; Oehl, R. S.; Petrillo, E. W., Jr. J. Med. Chem. 1995, 38, 4557. (g) Wroblewski, A. E.; Piotrowska, D. G. Tetrahedron 1998, 54, 8123.
20. (5)(a) Yokomatsu, T.; Yoshida, Y.; Suemune, K.; Yamagishi, T.; Shibuya, S. Tetrahedron: Asymmetry 1995, 6, 365. (b) Yokomatsu, T.; Suemune, K.; Yamagishi, T.; Shibuya, S. Synlett 1995, 847. (c) Kitamura, M.; Tokunaga, M.; Pham, T.; Lubell, W. D.; Noyori, R. Tetrahedron Lett. 1995, 36, 5769. Zygmunt, J.; Gancarz, R.; Lejczak, B.; Wieczorek, P.; Kafarski, P. Bioorg. Med. Chem. Lett. 1996, 6, 2989. (e) Bongini, A.; Camerini, R.; Hofman, S.; Panunzio, M. Tetrahedron Lett. 1994, 35, 8045. (f) Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E.; Free, C. A.; Rogers, W. L.; Smith, S. A.; DeForrest, J. M.; Oehl, R. S.; Petrillo, E. W., Jr. J. Med. Chem. 1995, 38, 4557. (g) Wroblewski, A. E.; Piotrowska, D. G. Tetrahedron 1998, 54, 8123.
21. (5)(a) Yokomatsu, T.; Yoshida, Y.; Suemune, K.; Yamagishi, T.; Shibuya, S. Tetrahedron: Asymmetry 1995, 6, 365. (b) Yokomatsu, T.; Suemune, K.; Yamagishi, T.; Shibuya, S. Synlett 1995, 847. (c) Kitamura, M.; Tokunaga, M.; Pham, T.; Lubell, W. D.; Noyori, R. Tetrahedron Lett. 1995, 36, 5769. Zygmunt, J.; Gancarz, R.; Lejczak, B.; Wieczorek, P.; Kafarski, P. Bioorg. Med. Chem. Lett. 1996, 6, 2989. (e) Bongini, A.; Camerini, R.; Hofman, S.; Panunzio, M. Tetrahedron Lett. 1994, 35, 8045. (f) Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E.; Free, C. A.; Rogers, W. L.; Smith, S. A.; DeForrest, J. M.; Oehl, R. S.; Petrillo, E. W., Jr. J. Med. Chem. 1995, 38, 4557. (g) Wroblewski, A. E.; Piotrowska, D. G. Tetrahedron 1998, 54, 8123.
22. (5)(a) Yokomatsu, T.; Yoshida, Y.; Suemune, K.; Yamagishi, T.; Shibuya, S. Tetrahedron: Asymmetry 1995, 6, 365. (b) Yokomatsu, T.; Suemune, K.; Yamagishi, T.; Shibuya, S. Synlett 1995, 847. (c) Kitamura, M.; Tokunaga, M.; Pham, T.; Lubell, W. D.; Noyori, R. Tetrahedron Lett. 1995, 36, 5769. Zygmunt, J.; Gancarz, R.; Lejczak, B.; Wieczorek, P.; Kafarski, P. Bioorg. Med. Chem. Lett. 1996, 6, 2989. (e) Bongini, A.; Camerini, R.; Hofman, S.; Panunzio, M. Tetrahedron Lett. 1994, 35, 8045. (f) Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E.; Free, C. A.; Rogers, W. L.; Smith, S. A.; DeForrest, J. M.; Oehl, R. S.; Petrillo, E. W., Jr. J. Med. Chem. 1995, 38, 4557. (g) Wroblewski, A. E.; Piotrowska, D. G. Tetrahedron 1998, 54, 8123.
23. (5)(a) Yokomatsu, T.; Yoshida, Y.; Suemune, K.; Yamagishi, T.; Shibuya, S. Tetrahedron: Asymmetry 1995, 6, 365. (b) Yokomatsu, T.; Suemune, K.; Yamagishi, T.; Shibuya, S. Synlett 1995, 847. (c) Kitamura, M.; Tokunaga, M.; Pham, T.; Lubell, W. D.; Noyori, R. Tetrahedron Lett. 1995, 36, 5769. Zygmunt, J.; Gancarz, R.; Lejczak, B.; Wieczorek, P.; Kafarski, P. Bioorg. Med. Chem. Lett. 1996, 6, 2989. (e) Bongini, A.; Camerini, R.; Hofman, S.; Panunzio, M. Tetrahedron Lett. 1994, 35, 8045. (f) Patel, D. V.; Rielly-Gauvin, K.; Ryono, D. E.; Free, C. A.; Rogers, W. L.; Smith, S. A.; DeForrest, J. M.; Oehl, R. S.; Petrillo, E. W., Jr. J. Med. Chem. 1995, 38, 4557. (g) Wroblewski, A. E.; Piotrowska, D. G. Tetrahedron 1998, 54, 8123.
24. (a) Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem.,Int. Ed. Engl. 1996, 35, 451. (b) Li, G.; Angert, H. H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2813.
25. (a) Li, G.; Chang, H.-T.; Sharpless, K. B. Angew. Chem.,Int. Ed. Engl. 1996, 35, 451. (b) Li, G.; Angert, H. H.; Sharpless, K. B. Angew. Chem., Int. Ed. Engl. 1996, 35, 2813.
26. We have recently been made aware that after our initial presentation of this work (Thomas, A. A.; Sharpless K. B. Abstracts of Papers; 213th National Meeting of the American Chemical Society, San Francisco, CA, Apr 13-17, 1997; American Chemical Society: Washington, DC, 1997; ORGN 126) another group published the preparation of α-hydroxy-β-toluenesulfonamidophosphonates by the AA: Cravotto, G.; Giovenzana, G. B.; Pagliarin, R.; Palmisano, G.; Sisti, M. Tetrahedron: Asymmetry 1998, 9, 745.
27. (a) Nieschalk, J.; Batsanov, A. S.; O'Hagan, D.; Howard, J. A. K. Tetrahedron 1996, 52, 165. (b) Burke, T. R., Jr.; Smyth, M. S.; Nomizu, M.; Otaka, A.; Roller, P. P. J. Org. Chem. 1993, 58, 1336.
28. (a) Nieschalk, J.; Batsanov, A. S.; O'Hagan, D.; Howard, J. A. K. Tetrahedron 1996, 52, 165. (b) Burke, T. R., Jr.; Smyth, M. S.; Nomizu, M.; Otaka, A.; Roller, P. P. J. Org. Chem. 1993, 58, 1336.
29. (a) Mikoiajczyk, M.; Grzejszczak, S.; Midura, W.; Zatorski, A. Synthesis 1976, 396. (b) For a review of vinylphosphonates, see: Minami, T.; Motoyoshiya, J. Synthesis 1992, 333.
30. (a) Mikoiajczyk, M.; Grzejszczak, S.; Midura, W.; Zatorski, A. Synthesis 1976, 396. (b) For a review of vinylphosphonates, see: Minami, T.; Motoyoshiya, J. Synthesis 1992, 333.
31. 31P NMR for crude 7a had numerous resonances (complicated by the fact that the starting olefin was not diasteromerically pure), and therefore, regioisomer assignments were not made.
32. 31P NMR was evident during formation of product 4a after only 4 h reaction time.
33. 31P NMR was evident during formation of product 4a after only 4 h reaction time.
34. 31P NMR was evident during formation of product 4a after only 4 h reaction time.
35. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991; Chapter 7.
36. O'Brien, P. Angew. Chem., Int. Ed. Engl. 1999, 38, 326.
37. Preliminary work using benzyl carbamate as the nitrogen source and the p-methoxystyrenyl phosphonate (entry 2, Table 1) indicated significantly poorer conversion than with ethyl carbamate (30-40% unreacted olefin). The reaction conditions are currently being optimized.
38. 13C NMR data of related α-amino and α-hydroxyphosphonates, see refs 4a and 5b, respectively. (16) One of the reviewers pointed out that the assignment of the urethane proton could be confused with the hydroxyl proton, thus indicating the opposite regioisomer. This is unlikely for two reasons. First, the hydroxyl proton resonance in these sulfonamide and carbamate AA products is considerably broadened, and often difficult to distinguish from the baseline. Second, the urethane proton in 7b (δ = 5.8-6.1 ppm dependent on concentration, d, J = 8.0 Hz) exhibits a similar chemical shift and coupling constant to that observed for the urethane proton in the mesylate 10b (δ = 5.9 ppm, d, J = 8.0 Hz), in which no hydroxyl proton is present.
39. 13C NMR data of related α-amino and α-hydroxyphosphonates, see refs 4a and 5b, respectively. (16) One of the reviewers pointed out that the assignment of the urethane proton could be confused with the hydroxyl proton, thus indicating the opposite regioisomer. This is unlikely for two reasons. First, the hydroxyl proton resonance in these sulfonamide and carbamate AA products is considerably broadened, and often difficult to distinguish from the baseline. Second, the urethane proton in 7b (δ = 5.8-6.1 ppm dependent on concentration, d, J = 8.0 Hz) exhibits a similar chemical shift and coupling constant to that observed for the urethane proton in the mesylate 10b (δ = 5.9 ppm, d, J = 8.0 Hz), in which no hydroxyl proton is present.
40. Backvall, J.-E.; Oshima, K.; Palermo, R. E.; Sharpless, K. B. J. Org. Chem. 1979, 44, 1953.
41. 31P NMR spectra of 9a gave no indication of diastereomers, which would have been generated had epimerization at C-1 or C-2 occurred during the two-step synthesis from 2a In order for racemization to have occurred, simultaneous loss of stereochemistry at both C-1 and C-2 would have had to take place.
42. (a) Kemp, J. E. G. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 7, p 469. (b) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Padwa, A., Eds.; Elsevier Science Ltd.: Oxford, 1996; Vol. 1, p 1. Padwa, A.; Murphree, S. S. Prog. Heterocycl. Chem. 1994, 6, 56.
43. (a) Kemp, J. E. G. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 7, p 469. (b) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Padwa, A., Eds.; Elsevier Science Ltd.: Oxford, 1996; Vol. 1, p 1. Padwa, A.; Murphree, S. S. Prog. Heterocycl. Chem. 1994, 6, 56.
44. (a) Kemp, J. E. G. Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford, 1991; Vol. 7, p 469. (b) Pearson, W. H.; Lian, B. W.; Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R., Rees, C. W., Scriven, E. F. V., Padwa, A., Eds.; Elsevier Science Ltd.: Oxford, 1996; Vol. 1, p 1. Padwa, A.; Murphree, S. S. Prog. Heterocycl. Chem. 1994, 6, 56.
45. Mintz, M. J.; Walling, C. Organic Syntheses; Wiley: New York, 1973; Collect. Vol. V, p 184.