Highly diastereoselective α-hydroxylation of fox chiral auxiliary-based amide enolates with molecular oxygen

Organic Letters

Volumn 12, Issue 7, 2010, Pages 1496-1499

  Lubin, Hodney ^a   Tessier, Arnaud ^a   Chaume, Grégory ^a   Pytkowicz, Julien ^a   Brigaud, Thierry B ^a  

^a Université Paris Seine   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMIDE; CARBOXYLIC ACID; KETONE; OXAZOLE DERIVATIVE; OXAZOLIDINE; OXYGEN;

ARTICLE; CHEMISTRY; CONFORMATION; HYDROXYLATION; STEREOISOMERISM; SYNTHESIS;

ALCOHOLS; AMIDES; CARBOXYLIC ACIDS; HYDROXYLATION; KETONES; MOLECULAR CONFORMATION; OXAZOLES; OXYGEN; STEREOISOMERISM;

EID: 77950289084     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100211s     Document Type: Article

References (53)

1. (a) Davis, F. A.; Chen, B.-C Chem. Rev. 1992, 92, 919-934.
2. (b) Coppola, G. M.; Schuster, H. F. α-Hydroxy acids in enantioselective synthesis; Wiley-VCH: Weinheim, 1997.
3. For general reviews, see: (a) Jones, A. B. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Ley, S. V., Ed.; Pergamon Press Ltd.: Oxford, 1991; Vol.7, pp 151-191.
4. (b) Chen, B.-C.; Zhou, P.; Davis, F. A.; Ciganek, E. In Organic Reactions; Overman L. E., Ed.; John Wiley & Sons Inc.: New York, 2003; Vol.62, pp 1-356.
5. Bailey, E. J.; Barton, D. H. R.; Elks, J.; Templeton, J. F. J. Chem. Soc. 1962, 1578-1591.
6. Gardner, J. N.; Carlon, F. E.; Gnoj, O. J. Org. Chem. 1968, 33, 3294-3297.
7. (a) Wasserman, H. H.; Lipshutz, B. H. Tetrahedron Lett. 1975, 27, 1731-1734.
8. (b) Kim, M. Y.; Starrett, J. E., Jr.; Weinreb, S. M. J. Org. Chem. 1981, 46, 5383-5389.
9. Williams, R. M.; Armstrong, R. W.; Dung, J.-S. J. Am. Chem. Soc. 1985, 107, 3253-3266.
10. Hartwig, W.; Born, L. J. Org. Chem. 1987, 52, 4352-4358.
11. (e) Adam, W.; Metz, M.; Prechtl, F.; Renz, M. Synthesis 1994, 563-566.
12. (a) Gardner, J. N.; Carlon, F. E.; Gnoj, O. J. Org. Chem. 1968, 33, 1566-1570.
13. (b) Avramoff, M.; Sprinzak, Y. J. Am. Chem. Soc. 1963, 85, 1655-1657.
14. Doering, W.; Von, E.; Haines, R. M. J. Am. Chem. Soc. 1954, 76, 482-486.
15. (a) Davis, F. A.; Sheppard, A. C. Tetrahedron 1989, 45, 5703-5742.
16. (b) Davis, F. A. J. Org. Chem. 2006, 71, 8993-9003.
17. (a) Vedejs, E. J. Am. Chem. Soc. 1974, 94, 5944-5946.
18. (b) Mimoun, H.; Seree de Roche, I.; Sajus, L. Bull. Soc. Chim. Fr. 1969, 1481-1492.
19. Vedejs, E.; Engler, D. A.; Telschow, J. E. J. Org. Chem. 1978, 43, 188-196.
20. Vedejs, E.; Martinez, G. R. J. Am. Chem. Soc. 1980, 102, 7994-7996.
21. (e) Vedejs, E.; Larsen, S. Org. Synth. 1986, 64, 127-137.
22. (f) Marin, J.; Didierjean, C.; Aubry, A.; Briand, J.-P.; Guichard, G. J. Org. Chem. 2002, 67, 8440-8449.
23. (a) Evans, D. A.; Morrissey, M. M.; Dorow, R. L. J. Am. Chem. Soc. 1985, 107, 4346-4348.
24. (b) Davis, F. A.; Vishawakarma, L. C. Tetrahedron Lett. 1985, 26, 3539-3542.
25. Gamboni, R.; Tamm, C. Helv. Chim. Acta 1986, 69, 615-620.
26. Enders, D.; Bhushan, V. Tetrahedron Lett. 1988, 29, 2437-2440.
27. (a) Davis, F. A.; Haque, M. S.; Ulatowski, T. G.; Towson, J. J. Org. Chem. 1986, 51, 2402-2404.
28. (b) Davis, F. A.; Haque, M. S. J. Org. Chem. 1986, 51, 4083-4085.
29. Davis, F. A.; Ulatowski, T. G.; Haque, M. S. J. Org. Chem. 1987, 52, 5288-5290.
30. Davis, F. A.; Weismiller, M. C.; Sankar Lal, G.; Chen, B.-C.; Prezslawski, R. M. Tetrahedron Lett. 1989, 30, 1613-1616.
31. (e) Davis, F. A.; Weismiller, M. C.; Murphy, C. K.; Reddy, R. T.; Chen, B.-C. J. Org. Chem. 1992, 57, 7274-7285.
32. (a) Ishimaru, T.; Shibata, N.; Nagai, J.; Nakamura, S.; Toru, T.; Kanemasa, S. J. Am. Chem. Soc. 2006, 128, 16488-16489.
33. (b) Brown, S. P.; Brachu, M. P.; Sinz, C. J.; MacMillan, D. W. C. J. Am. Chem. Soc. 2003, 125, 10808-10809.
34. Adam, W.; Lazarus, M.; Saha-Moller, C. R.; Schreier, P. Acc. Chem. Res. 1999, 32, 837-845.
35. For recent examples, see: (a) Raghavan, S.; Subramanian, S. G.; Tony, K. A. Tetrahedron Lett. 2008, 49, 1601-1604.
36. (b) Kaliappan, K. P.; Gowrisankar, P. Synlett 2007, 1537-1540.
37. Monma, S.; Sunazuka, T.; Nagai, K.; Arai, T.; Shiomi, K.; Matsui, R.; Ohmura, S. Org. Lett. 2006, 8, 5601-5604.
38. Pichlmair, S.; de Lera Ruiz, M.; Vilotijevic, I.; Paquette, L. A. Tetrahedron 2006, 62, 5791-5802.
39. (e) Gaich, T.; Karig, G.; Martin, H. J.; Mulzer, J. Eur. J. Org. Chem. 2006, 3372-3394.
40. Adam, W.; Metz, M.; Prechtl, F.; Renz, M. Synthesis 1994, 563-566.
41. Tessier, A.; Pytkowicz, J.; Brigaud, T. Angew. Chem., Int. Ed. 2006, 45, 3677-3681.
42. Sini, G.; Tessier, A.; Pytkowicz, J.; Brigaud, T. Chem.-Eur. J. 2008, 14, 3363-3370.
43. Tessier, A.; Lahmar, N.; Pytkowicz, J.; Brigaud, T. J. Org. Chem. 2008, 73, 3970-3973.
44. The hydroperoxide 4 was conveniently isolated after aqueous workup, but it decomposed over silica gel.
45. These diastereoselectivities are comparable or better to those generally achieved by the alternative approach involving the chiral auxiliarybased alkylations of benzyloxyacetyl amides. (a) Crimmins, M. T.; Emmitte, K. A.; Katz, J. D. Org. Lett. 2000, 2, 2165-2167, and references cited therein.
46. (b) Chun, C. C.; Lee, G.-J.; Kim, J. N.; Kim, T H. Tetrahedron: Asymmetry 2005, 2989-2992.
47. Sodium, enolate of the (S)-4-isopropyl-3-propionyl-1,3-oxazolidin-2-one.
48. Kihara, N.; Ollivier, C.; Renaud, P. Org. Lett. 1999, 1, 1419-1422.
49. For a previously reported similar reduction of SuperQuat amide into hemiaminal, see: Davies, S. G.; Nicholson, R. L.; Smith, A. D. Org, Biomol. Chem. 2005, 3, 348-359.
50. (a) Nakata, M.; Arai, M.; Tomooka, K.; Ohsawa, N.; Kinoshita, M. Bull. Chem. Soc. Jpn. 1989, 62, 2618-2635.
51. (b) Fuganti, C.; Grasselli, P.; Spreafico, R.; Zirotti, C. J. Org. Chem. 1984, 49, 543-546.
52. Cardillo, G. Tetrahedron 1989, 45, 1501-1508.
53. Compound 11 was prepared by electrophilic iodination of the sodium enolate of la with N-iodosuccinimide.