Highly diastereoselective anti-aldol reactions of glycolate titanium enolates

Journal of Organic Chemistry

Volumn 74, Issue 4, 2009, Pages 1788-1790

  Gawas, Dnyaneshwar ^a   Kazmaier, Uli ^a  

^a SAARLAND UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

6 [[1 (3,4 DIHYDRO 8 HYDROXY 1 OXO 1H 2 BENZOPYRAN 3 YL) 3 METHYLBUTYL]AMINO] 4,5 DIHYDROXY 6 OXO 3 AMMONIOHEXANOATE; ANTIBIOTIC AGENT; CARBOHYDRATE; CARBONYL DERIVATIVE; GLYCOLIC ACID DERIVATIVE; NATURAL PRODUCT; RAPAMYCIN; TARTROLON B; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; CHROMATOGRAPHY; DIASTEREOISOMER; ORGANIC CHEMISTRY; STEREOCHEMISTRY;

ALCOHOLS; ALDEHYDES; CHELATING AGENTS; GLYCOLATES; ORGANOMETALLIC COMPOUNDS; STEREOISOMERISM; SUBSTRATE SPECIFICITY; TITANIUM;

EID: 64349108339     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo8025466     Document Type: Article

References (60)

1. Nielsen, A. T.; Houlihan, W. J. Organic Reactions; Wiley: New York, 1968; Vol. 16.
2. (a) Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976. 98, 2868-2877.
3. (a) Heathcock, C. H.; White, C. T. J. Am. Chem. Soc. 1979, 101, 7076-7077.
4. (b) Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984; Vol. 3, Part B, Chapter 2.
5. (a) Evans, D. A.; Takacs, J. M.; McGee, L. R.; Ennis, M. D.; Mathre, D. J.; Bartroli, J. J. Pure Appl. Chem. 1981, 53, 1109-1127.
6. (b) Evans, D. A.; Nelson, J. V.; Taber, T. R. Top. Stereochem. 1982, 13, 1-115.
7. (a) Masamune, S.; Choy, W.; Petersen, J. S.; Sita, L. R. Angew. Chem. 1985, 97, 1-30; Angew. Chem., Int. Ed. Engl. 1985, 24,1-30.
8. (b) Braun, M. In Advance in Carbanion Chemistry; Snieckus, V., Ed.; JAI Press: Greenwich, 1992; Vol. 1.
9. Ireland, R. E.; Willard, A. K. Tetrahedron Lett. 1975, 3975-3978.
10. Heathcock, C. H.; Buse, C. T.; Kleschik, W. A.; Pirrung, M. C.; Sohn, J. E.; Lampe, J. J. Org. Chem. 1980, 45, 1066-1081.
11. Mekelburger, H. B.; Wilcox C. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming I., Eds.; Pergamon Press: New York, 1991; Vol. 2, p 101ff.
12. (a) Evans, D. A.; Bender, S. L.; Morris, J. J. Am. Chem. Soc. 1988, 110, 2506-2526.
13. (b) Ku, T. W.; Kondrad, K. H.; Gelason, J. G. J. Org. Chem. 1989, 54, 3487-3491.
14. (c) Andrus, M. B.; Schreiber, S. L. J. Am. Chem. Soc. 1993, 115, 10420-10421.
15. (d) Evans, D. A.; Barrow, J. C.; Leighton, J. L.; Robichaud, A. J.; Sefkow, M. J. Am. Chem. Soc. 1994, 116, 12111-12112.
16. (e) Rudge, A. J.; Collins, I.; Holmes, A. B.; Baker, R. Angew. Chem. 1994, 106, 2416-2418; Angew Chem., Int. Ed. Engl. 1994, 33, 2320-2322.
17. (f) Martin, S. F.; Dodge, J. A.; Burgess, L. E.; Limberakis, C.; Hartmann, M. Tetrahedron 1996, 52, 3229-3246.
18. (g) Crimmins, M. T.; Choy, A. L. J. Org. Chem. 1997, 62, 7548-7549.
19. (h) Nakamura, Y.; Hirata, M.; Kuwano, E.; Taniguchi, E. Biosci. Biotechnol. Biochem. 1998, 62, 1550-1554.
20. (i) Crimmins, M. T.; Choy, A. L. J. Am. Chem. Soc. 1999, 121, 5653-5660.
21. (j) Haight, D.; Birrell, H. C.; Cantello, B. C. C.; Eggleston, D. S.; Haltiwanger, R. C.; Hindley, R. M.; Ramaswany, A.; Stevens, N. C. Tetrahedron: Asymmetry 1999, 10, 1353-1367.
22. anti-Aldol reactions: (k) Danda, H.; Hansen, M. M.; Heathcock, C. H. J. Org. Chem. 1990, 55, 173-181.
23. anti-Glycolate: (l) Evans, D. A.; Kaldor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001-7031.
24. (m) Evans, D. A.; Gage, J. R.; Leighton, J. L.; Kim, A. S. J. Org. Chem. 1992, 57, 1961-1963.
25. (n) Evans, D. A.; Weber, A. E. J. Am. Chem. Soc. 1986, 108, 6757-6761.
26. (o) Saika, H.; Fruh, T.; Iwasaki, G.; Koizumi, S.; Mori, I.; Hayakawa, K. Bioorg. Med. Chem. Lett. 1993, 3, 2129-2134.
27. (p) Li, Z.; Wu, R.; Michalczyk, R.; Dunlap, R. B.; Odom, J. D.; Silks, L. A., III. J. Am. Chem. Soc. 2000, 122, 386-387.
28. Diastereoselective Ti glycolate: (q) Annunziata, R.; Cinquini, M.; Cozzi, F.; Borgia, A. L. J. Org. Chem. 1992, 57, 6339-6342.
29. (a) Vezina, C.; Kudelski, A.; Sehgal, S. N. J. Antibiot. 1975, 28, 721-726.
30. (b) Nicolaou, K. C.; Chakraborty, T. K.; Piscopio, A. D.; Minowa, N.; Bertinato, P. J. Am. Chem. Soc. 1993, 115, 4419-4420.
31. (a) Shimojima, Y.; Hayashi, H.; Ooka, T.; Shibukawa, M.; Iitaka, Y. Tetrahedron Lett. 1982, 23, 5435-5438.
32. (b) Shimojima, Y.; Hayashi, H. J. Med. Chem. 1983, 26, 1370.
33. (c) Shimojima, Y.; Hayashi, H.; Ooka, T.; Shibukawa, M.; Iitaka, Y. Tetrahedron 1984, 40, 2519-2527.
34. Mulzer, J.; Berger, M. Tetrahedron Lett. 1998, 39, 803-806.
35. Pearson, W. H.; Cheng, M. C. J. Org. Chem. 1987, 52, 3176-3178.
36. Andrus, M. B.; Somasekhar, B. V.; Meredith, E. L.; Dalley, N. K. Org. Lett. 2000, 2, 3035-3037.
37. Scholtis, S.; Ide, A.; Mahrwald, R. Org. Lett. 2006, 8, 5353-5355.
38. Denmark, S. E.; Chung, W.-J. J. Org. Chem. 2008, 73, 4582-4595.
39. (a) Kazmaier, U.; Grandel, R. Synlett 1995, 945-946.
40. (b) Grandel, R.; Kazmaier, U.; Nuber, B. Liebigs Ann. 1996, 1143-1150.
41. (c) Grandel, R.; Kazmaier, U. Tetrahedron Lett. 1997, 38, 8009-8012.
42. (d) Grandel, R.; Kazmaier, U. Eur. J. Org. Chem. 1998, 409-417.
43. (e) Grandel, R.; Kazmaier, U. J. Org. Chem. 1998, 63, 4524-4528.
44. (f) Kazmaier, U.; Grandel, R. Eur. J. Ore. Chem. 1998, 1833-1840.
45. (g) Kummeter, M.; Kazmaier, U. Eur. J. Org. Chem. 2003, 3325-3329.
46. (h) Kummeter, M.; Kazmaier, U. Eur. J. Org. Chem. 2003, 3330-3334.
47. (a) Kazmaier, U. Amino Acids 1996, 11, 283-299.
48. (b) Kazmaier, U. Recent Res. Dev. Ore. Chem. 1998, 2, 351-358.
49. (c) Kazmaier, U. Bioorganic Chemistry; Wiley-VCH: Weinheim, Germany, 1999; pp 201-206.
50. (a) Kazmaier, U.; Schau/3, D.; Raddatz, S.; Pohlman, M. Chem. Eur. J. 2001, 7, 456-464.
51. (b) Kazmaier, U.; Zumpe, F. L. Eur. J. Org. Chem. 2001, 4067-4076.
52. (c) Pohlman, M.; Kazmaier, U. Org. Lett. 2003, 5, 2631-2633.
53. (d) Mendler, B.; Kazmaier, U. Org. Lett. 2005, 7, 1715-1718.
54. (e) Mendler, B.; Kazmaier, U.; Huch, V.; Veith, M. Org. Lett. 2005, 7, 2643-2646.
55. (f) Kazmaier, U.; Kramer, K. J. Org. Chem. 2006, 71, 8950-8953.
56. In comparison, zinc enolates give by far the best results in reactions of amino acid esters (see ref 18).
57. No second stereo isomer could be detected by GC.
58. Denmark, S. E.; Henke, B. R. J. Am. Chem. Soc. 1991, 113, 2177-2194.
59. Fellman, P.; Dubois, J. E. Tetrahedron 1978, 34, 1349-1357.
60. Heathcock, C. H.; Pirrung, M. C.; Young, S. D.; Hagen, J. P.; Jarvi, E. T.; Badertscher, U.; Marki, H. P.; Montgomery, S. H. J. Am. Chem. Soc. 1984, 106, 8161-8174.