Anti-selective glycolate aldol additions with an oxapyrone boron enolate

Organic Letters

Volumn 2, Issue 19, 2000, Pages 3035-3037

  Andrus, Merritt B ^a   Sekhar, B B V Soma ^a   Meredith, Erik L ^a   Dalley, N Kent ^a  

^a Brigham Young University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; BORON DERIVATIVE; GLYCOL; GLYCOLIC ACID DERIVATIVE; PYRONE DERIVATIVE;

ARTICLE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALDEHYDES; BORON COMPOUNDS; GLYCOLATES; GLYCOLS; PYRONES; STEREOISOMERISM;

EID: 0034699265     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0002166     Document Type: Article

References (63)

1. Syn versions: (a) Evans, D. A.; Bender, S. L.; Morris, J. J. Am. Chem. Soc. 1988, 110, 2506.
2. (b) Ku, T. W.; Kondrad, K. H.; Gleason, J. G. J. Org. Chem. 1989, 54, 3487.
3. (c) Andrus, M. B.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10420.
4. Anti: (d) Danda, H.; Hansen, M. M.; Heathcock, C. H. J. Org. Chem. 1990, 55, 173.
5. Anti glycolate: (e) Evans, D. A.; Kaldor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001.
6. (f) Evans, D. A.; Gage, J. R.; Leighton, J. L.; Kim, A. S. J. Org. Chem. 1992, 57, 1961.
7. (g) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1986, 108, 6757.
8. (h) Saika, H.; Fruh, T.; Iwasaki, G.; Koizumi, S.; Mori, I.; Hayakawa, K. Bioorg. Med. Chem. Lett. 1993, 3, 2129.
9. (i) Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A., III J. Am. Chem. Soc. 2000, 122, 386.
10. Diastereoselective Ti glycolate: (j) Annunziata, R.; Cinquini, M.; Cozzi, F.; Borgia, A. L. J. Org. Chem. 1992, 57, 6339.
11. (a) German, C. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 2.4.
12. (b) Evans, D. A.; Murry, J. A.; Kozlowski, M. C. J. Am. Chem. Soc. 1996, 118, 5814.
13. (c) Hattori, K.; Yamamoto, H. J. Org. Chem. 1993, 58, 5301.
14. (a) Abiko, A.; Liu, J.-F.; Masamune, S. J. Am. Chem. Soc. 1997, 119, 2586.
15. (b) Ghosh, Arun, K.; Onishi, M. J. Am. Chem. Soc. 1996, 118, 2527.
16. (c) Paterson, I.; Wren, S. P. J. Chem. Soc., Chem. Commun. 1993, 1790.
17. (d) Gennari, C.; Moresca, D.; Vieth, S.; Vulpetti, A. Angew. Chem., Int. Ed. Engl. 1993, 32, 1618.
18. (e) Meyers, A. G.; Widdowson, K. L. J. Am. Chem. Soc. 1990, 112, 9672.
19. (f) Corey, E. J.; Kim, S. S. J. Am. Chem. Soc. 1990, 112, 4976.
20. (g) Gennari, C.; Bernardi, A.; Colombo, L.; Scolastico, C. J. Am. Chem. Soc. 1985, 107, 5812.
21. (h) Meyers, A. I.; Yamamoto, Y. Tetrahedron 1984, 40, 2309.
22. Glycolate versions of the norephendrine Masamune auxiliary give syn aldol products: Andrus, M. B.; Turner, T. M. Unpublished results.
23. (a) Paterson, I.; Tillyer, R. D. J. Org. Chem. 1993, 58, 4182.
24. (b) Cameron, J. C.; Paterson, I. Org. React. 1997, 51, 1.
25. (c) Paterson, I.; Wallace, D. J.; Cowden, C. J. Synthesis 1998, 639.
26. (a) Kobayashi, S.; Kawasuji, T. Tetrahedron Lett. 1994, 35, 3329.
27. (b) Kobayashi, S.; Hayashi, T. J. Org. Chem. 1995, 60, 1098.
28. Gennari, C.; Vulpetti, A.; Pain, G. Tetrahedron 1997, 53, 5909.
29. Carda, M.; Falomir, E.; Murga, J.; Castillo, E.; Gonzalez, F.; Marco, J. A. Tetrahedron Lett. 1999, 40, 6845.
30. (a) Wang, L.; Sharpless, K. B. J. Am. Chem. Soc. 1992, 114, 7568.
31. (b) Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 4, 2483.
32. Syn selective: (a) Hoffmann, R. W.; Kemper, B. Tetrahedron Lett. 1980, 4883.
33. (b) Wuts, P. G. M.; Bigelow, S. S.; J. Chem. Soc., Chem. Commun. 1984, 736.
34. (c) Roush, W. R.; Michaelides, M. R. Tetrahedron Lett. 1986, 27, 3353.
35. (d) Keck, G. E.; Abbott, D. E.; Wiley: M. R. Tetrahedron Lett. 1987, 28, 139.
36. (e) Koreeda, M.; Tanaka, Y. Tetrahedron Lett. 1987, 28, 143.
37. (f) Brown, H. C.; Jadhav, K. P.; Bhat, K. S. J. Am. Chem. Soc. 1988, 110, 1535.
38. (g) Marshall, J. A.; Gung, W. Y. Tetrahedron Lett. 1989, 30, 2183.
39. Anti undifferentiated diols from silylallylboranates: (h) Roush, W. R.; Grover, P. T.; Lin, X. Tetrahedron Lett. 1990, 31, 7563.
40. Marshall, J. A.; Hinkle, K. W. J. Org. Chem. 1995, 60, 1920.
41. (a) Seebach, D.; Naef, R. Helv. Chim. Acta 1981, 64, 2704.
42. (b) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1987, 52, 3176.
43. (c) Greiner, A.; Ortholand, J.-Y. Tetrahedron Lett. 1990, 31, 2135.
44. (d) Reno, D. S.; Lotz, B. T.; Miller, M. J. Tetrahedron Lett. 1990, 31, 827.
45. (e) Majewski, M.; Gleave, D. M.; Nowak, P. Can. J. Chem. 1995, 73, 1616.
46. (f) Fairbanks, A. J.; Sinay, P. Tetrahedron Lett. 1995, 36, 893.
47. (g) Comins, D. L.; Kuethe, J. T.; Hong, H.; Lakner, F. J. J. Am. Chem. Soc. 1999, 121, 2651.
48. (h) Chang, J.-W.; Jang, D.-P.; Uang, B.-J.; Liao, F.-L.; Wang, S.-L. Org. Lett. 1999, 1, 2061.
49. Sharpless, K. B.; Amberg, W.; Bennami, Y. L.; Crispino, G. A.; Hartung, J.; Jeong, K.; Kwong, H.; Morikawa, K.; Wang Z. Xu, D.; Zhang, X. J. Org. Chem. 1992, 57, 2768.
50. (a) Burke, S. D.; Sametz, G. M. Org. Lett. 1999, 1, 71.
51. (b) David, S.; Thieffry, A.; Veyrieres, A. J. Chem. Soc., Perkin Trans. 1 1981, 1796.
52. (a) Brown, H. C.; Ganesan, K.; Dhar, R. K. J. Org. Chem. 1993, 58, 147.
53. (b) Brown, H. C.; Dhar, R. K.; Ganesan, K.; Singaram, B. J. Org. Chem. 1992, 57, 499.
54. Paterson, I.; Wallace, D.; Cowden, C. Synthesis 1998, 639.
55. 1 = 0.0424 [I > 2σ(I)] (see Supporting Information).
56. α,OH = 6-9 Hz.
57. (a) Zimmerman, H. E.; Traxler, M. D. J. Am. Chem. Soc. 1957, 79, 1920.
58. (b) Fenzl, W.; Koster, R. J. Liebigs Ann. Chem. 1975, 1322.
59. (c) Masamune, S. Aldrichimica Acta 1978, 11, 23.
60. (a) Danda, H.; Hansen, M. M.; Heathcock, C. H. J. Org. Chem. 1990, 55, 173.
61. (b) Raimundo, B. C.; Heathcock, C. H. Synlett 1990, 1213.
62. Wallace, T. W.; Wardell, I.; Li, K.-D.; Leeming, P.; Redhouse, A. D.; Challard, S. R. J. Chem. Soc., Perkin Trans. 1 1995, 2293.
63. (5S)-5-Phenyl[1, 4]dioxan-2-one 8 was prepared in five steps and 33% overall yield from (S)-mandelic acid as follows: LAH reduction of (S)-mandelic acid (Mosher, H. S.; Dale, J. A. J. Org. Chem. 1970, 35, 4002) gave (S)-phenylethylene glycol. Selective protection of the 1° alcohol as the TBDPS ether was followed by alkylation of the 2° alcohol by treatment with NaH and tert-butyl bromoacetate. Deprotection using TBAF and treatment with catalytic TFA provided 8.