Stereoselectivity in aldol reactions of chiral N-acyl selones

Journal of the American Chemical Society

Volumn 122, Issue 2, 2000, Pages 386-387

  Li, Zizhong ^a   Wu, Ruilian ^a   Michalczyk, Ryszard ^a   Dunlap, R Bruce ^b   Odom, Jerome D ^b   Silks III, Louis A ^a  

^a LOS ALAMOS NATIONAL LABORATORY   (United States)

^b UNIVERSITY OF SOUTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 OXAZOLIDINONE DERIVATIVE; ACID; ALDEHYDE; BORON; CARBON; CARBONYL DERIVATIVE; SELENIUM; TITANIUM;

ACYLATION; ARTICLE; CATALYSIS; CHELATION; CHEMICAL BOND; CHEMICAL REACTION; DERIVATIZATION; ISOMER; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033955174     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992702y     Document Type: Article

References (32)

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11. Silks, L. A.; Dunlap, R. B.; Odom, J. D. J. Am. Chem. Soc. 1990, 112, 4979. Silks, L. A.; Peng, J.; Odom, J. D.; Dunlap, R. B. J. Chem. Soc., Perkins Trans. 1 1991, 2495. Silks, L. A.; Peng, J.; Dunlap, R. B.; Odom, J. D. J. Org. Chem. 1991, 56, 6733. Peng, J.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Tetrahedron Asymmetry 1994, 5 (9), 1627. Peng, J.; Ashburn, D. A.; Barr, M. E.; Lebioda, L.; Martinez, R. A.; Garber, A. R.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. J. Org. Chem. 1995, 60 (17), 5540. Wu, R.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Tetrahedron Asymmetry 1995, 6 (4), 833. Wu, R.; Silks, L. A.; Odom, J. D.; Dunlap, R. B. Spectroscopy 1996, 11 (6), 37. Wu, R.; Hernández, G.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Chem. Commun. 1996, (10), 1125. Wu, R.; Barr, M. E.; Hernandez, G.; Silks, L. A. Rec. Res. Dev. Org. Bioorg. Chem. 1998, 2, 29. Wu, R.; Odom, J. D.; Dunlap, R. B.; Silks, L. A Tetrahedron Asymmetry 1999, 10 (8), 1465.
12. Silks, L. A.; Dunlap, R. B.; Odom, J. D. J. Am. Chem. Soc. 1990, 112, 4979. Silks, L. A.; Peng, J.; Odom, J. D.; Dunlap, R. B. J. Chem. Soc., Perkins Trans. 1 1991, 2495. Silks, L. A.; Peng, J.; Dunlap, R. B.; Odom, J. D. J. Org. Chem. 1991, 56, 6733. Peng, J.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Tetrahedron Asymmetry 1994, 5 (9), 1627. Peng, J.; Ashburn, D. A.; Barr, M. E.; Lebioda, L.; Martinez, R. A.; Garber, A. R.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. J. Org. Chem. 1995, 60 (17), 5540. Wu, R.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Tetrahedron Asymmetry 1995, 6 (4), 833. Wu, R.; Silks, L. A.; Odom, J. D.; Dunlap, R. B. Spectroscopy 1996, 11 (6), 37. Wu, R.; Hernández, G.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Chem. Commun. 1996, (10), 1125. Wu, R.; Barr, M. E.; Hernandez, G.; Silks, L. A. Rec. Res. Dev. Org. Bioorg. Chem. 1998, 2, 29. Wu, R.; Odom, J. D.; Dunlap, R. B.; Silks, L. A Tetrahedron Asymmetry 1999, 10 (8), 1465.
13. Silks, L. A.; Dunlap, R. B.; Odom, J. D. J. Am. Chem. Soc. 1990, 112, 4979. Silks, L. A.; Peng, J.; Odom, J. D.; Dunlap, R. B. J. Chem. Soc., Perkins Trans. 1 1991, 2495. Silks, L. A.; Peng, J.; Dunlap, R. B.; Odom, J. D. J. Org. Chem. 1991, 56, 6733. Peng, J.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Tetrahedron Asymmetry 1994, 5 (9), 1627. Peng, J.; Ashburn, D. A.; Barr, M. E.; Lebioda, L.; Martinez, R. A.; Garber, A. R.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. J. Org. Chem. 1995, 60 (17), 5540. Wu, R.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Tetrahedron Asymmetry 1995, 6 (4), 833. Wu, R.; Silks, L. A.; Odom, J. D.; Dunlap, R. B. Spectroscopy 1996, 11 (6), 37. Wu, R.; Hernández, G.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Chem. Commun. 1996, (10), 1125. Wu, R.; Barr, M. E.; Hernandez, G.; Silks, L. A. Rec. Res. Dev. Org. Bioorg. Chem. 1998, 2, 29. Wu, R.; Odom, J. D.; Dunlap, R. B.; Silks, L. A Tetrahedron Asymmetry 1999, 10 (8), 1465.
14. Silks, L. A.; Dunlap, R. B.; Odom, J. D. J. Am. Chem. Soc. 1990, 112, 4979. Silks, L. A.; Peng, J.; Odom, J. D.; Dunlap, R. B. J. Chem. Soc., Perkins Trans. 1 1991, 2495. Silks, L. A.; Peng, J.; Dunlap, R. B.; Odom, J. D. J. Org. Chem. 1991, 56, 6733. Peng, J.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Tetrahedron Asymmetry 1994, 5 (9), 1627. Peng, J.; Ashburn, D. A.; Barr, M. E.; Lebioda, L.; Martinez, R. A.; Garber, A. R.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. J. Org. Chem. 1995, 60 (17), 5540. Wu, R.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Tetrahedron Asymmetry 1995, 6 (4), 833. Wu, R.; Silks, L. A.; Odom, J. D.; Dunlap, R. B. Spectroscopy 1996, 11 (6), 37. Wu, R.; Hernández, G.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Chem. Commun. 1996, (10), 1125. Wu, R.; Barr, M. E.; Hernandez, G.; Silks, L. A. Rec. Res. Dev. Org. Bioorg. Chem. 1998, 2, 29. Wu, R.; Odom, J. D.; Dunlap, R. B.; Silks, L. A Tetrahedron Asymmetry 1999, 10 (8), 1465.
15. Silks, L. A.; Dunlap, R. B.; Odom, J. D. J. Am. Chem. Soc. 1990, 112, 4979. Silks, L. A.; Peng, J.; Odom, J. D.; Dunlap, R. B. J. Chem. Soc., Perkins Trans. 1 1991, 2495. Silks, L. A.; Peng, J.; Dunlap, R. B.; Odom, J. D. J. Org. Chem. 1991, 56, 6733. Peng, J.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Tetrahedron Asymmetry 1994, 5 (9), 1627. Peng, J.; Ashburn, D. A.; Barr, M. E.; Lebioda, L.; Martinez, R. A.; Garber, A. R.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. J. Org. Chem. 1995, 60 (17), 5540. Wu, R.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Tetrahedron Asymmetry 1995, 6 (4), 833. Wu, R.; Silks, L. A.; Odom, J. D.; Dunlap, R. B. Spectroscopy 1996, 11 (6), 37. Wu, R.; Hernández, G.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Chem. Commun. 1996, (10), 1125. Wu, R.; Barr, M. E.; Hernandez, G.; Silks, L. A. Rec. Res. Dev. Org. Bioorg. Chem. 1998, 2, 29. Wu, R.; Odom, J. D.; Dunlap, R. B.; Silks, L. A Tetrahedron Asymmetry 1999, 10 (8), 1465.
16. Silks, L. A.; Dunlap, R. B.; Odom, J. D. J. Am. Chem. Soc. 1990, 112, 4979. Silks, L. A.; Peng, J.; Odom, J. D.; Dunlap, R. B. J. Chem. Soc., Perkins Trans. 1 1991, 2495. Silks, L. A.; Peng, J.; Dunlap, R. B.; Odom, J. D. J. Org. Chem. 1991, 56, 6733. Peng, J.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Tetrahedron Asymmetry 1994, 5 (9), 1627. Peng, J.; Ashburn, D. A.; Barr, M. E.; Lebioda, L.; Martinez, R. A.; Garber, A. R.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. J. Org. Chem. 1995, 60 (17), 5540. Wu, R.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Tetrahedron Asymmetry 1995, 6 (4), 833. Wu, R.; Silks, L. A.; Odom, J. D.; Dunlap, R. B. Spectroscopy 1996, 11 (6), 37. Wu, R.; Hernández, G.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. Chem. Commun. 1996, (10), 1125. Wu, R.; Barr, M. E.; Hernandez, G.; Silks, L. A. Rec. Res. Dev. Org. Bioorg. Chem. 1998, 2, 29. Wu, R.; Odom, J. D.; Dunlap, R. B.; Silks, L. A Tetrahedron Asymmetry 1999, 10 (8), 1465.
17. Peng, J.; Barr, M.; Ashburn, D. A.; Odom, J. D.; Dunlap, R. B.; Silks, L. A. J. Org. Chem. 1994, 59, 4977.
18. Crimmins, M. T.; King, B. W.; Tabet, E. A. J. Am. Chem. Soc. 1997, 119, 7883.
19. Yan, T.-H.; Jung, A.-W.; Lee, H.-C.; Chang, C.-S.; Liu, W.-H. J. Org. Chem. 1995, 60, 3301 and references therein.
20. 4 (1.1 equiv) was added dropwise at -15°C. This mixture was stirred for 5 min, followed by the dropwise addition of DIPEA (1.15 equiv). The solution was stirred for an additional 30 min then cooled to -78°C, and 1.2 equiv of the aldehyde was added. The reaction mixture was stirred for the appropriate amount of time (Table 1). The reaction was quenched with 2 mL of methanol. Filtration through a pad of silica gel, followed by washing with a 40% ethyl acetate/toluene mixture (v/v), afforded a bright yellow solution. The ethyl acetate/toluene mixture effects the azeotropic removal of methanol. Carrying out the concentration step without toluene gives rise to a solution highly enriched with methanol, which causes decomposition of the selone adducts (red precipitate forms). Flash silica gel chromatography can be visually monitored because all of the aldol selone adducts prepared to dale are bright yellow.
21. 1H DQF-COSY NMR solution experiments to help ascertain the enolate geometry.
22. erythro(3-6 Hz). See: Wang, Y.-C.; Su, D.-W.; Lin, C.-M.; Tseng, H.-L.; Li, C-L.; Yan, T.-H. J. Org. Chem. 1999, 64, 6495 and references therein.
23. 2 with a protected D-glyceraldehyde (a Mukaiyama reaction) to give rise to the anti alcohol with 8:1 diastereoselectivity. See: Burke, S. D.; Jian, H.; Mongin, A. P. Tetrahedron Lett. 1998, 39, 2239.
24. 2 with a protected D-glyceraldehyde (a Mukaiyama reaction) to give rise to the anti alcohol with 8:1 diastereoselectivity. See: Burke, S. D.; Jian, H.; Mongin, A. P. Tetrahedron Lett. 1998, 39, 2239.
25. 2 with a protected D-glyceraldehyde (a Mukaiyama reaction) to give rise to the anti alcohol with 8:1 diastereoselectivity. See: Burke, S. D.; Jian, H.; Mongin, A. P. Tetrahedron Lett. 1998, 39, 2239.
26. 2 with a protected D-glyceraldehyde (a Mukaiyama reaction) to give rise to the anti alcohol with 8:1 diastereoselectivity. See: Burke, S. D.; Jian, H.; Mongin, A. P. Tetrahedron Lett. 1998, 39, 2239.
27. 2 with a protected D-glyceraldehyde (a Mukaiyama reaction) to give rise to the anti alcohol with 8:1 diastereoselectivity. See: Burke, S. D.; Jian, H.; Mongin, A. P. Tetrahedron Lett. 1998, 39, 2239.
28. 3)]. Rychnovsky, S. D.; Hoye, R. C. J. Am Chem. Soc. 1994, 116, 1753.
29. 3)]. Rychnovsky, S. D.; Hoye, R. C. J. Am Chem. Soc. 1994, 116, 1753.
30. 4 in THF at 0°C gave rise to the 1,3 diol.
31. 2 with aldehydes, see: Evans, D. A.; Halstead, D. P.; Allison, B. D. Tetrahedron Lett. 1990, 40, 4461. Evans, D. A.; Allison, B. D.; Yang, M. G. Tetrahedron Lett. 1999, 40, 4457.
32. 2 with aldehydes, see: Evans, D. A.; Halstead, D. P.; Allison, B. D. Tetrahedron Lett. 1990, 40, 4461. Evans, D. A.; Allison, B. D.; Yang, M. G. Tetrahedron Lett. 1999, 40, 4457.