(S)- or (R)-3-(E-enoyl)-4-phenyl-1,3-oxazolidin-2-ones: Ideal Michael acceptors to afford a virtually complete control of simple and face diastereoselectivity in addition reactions with glycine derivatives

Organic Letters

Volumn 2, Issue 6, 2000, Pages 747-750

  Soloshonok, Vadim A ^a   Cai, Chaozhong ^a   Hruby, Victor J ^a  

^a University of Arizona   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; GLYCINE; OXAZOLE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM;

GLYCINE; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; OXAZOLES; STEREOISOMERISM;

EID: 0034704633     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990402f     Document Type: Article

References (37)

1. (a) Oare D. A.; Heathcock, C. H. Topics in Stereochemistry; Eliel, E. L., Wilen, S. H., Eds.; Wiley: New York, 1990; Vol. 19, pp 227-407.
2. (b) Oare, D. A.; Henderson, M. A.; Sanner, M. A.; Heathcock, C. H. J. Org. Chem. 1990, 55, 132.
3. For reviews, see: (a) Duthaler, R. O. Tetrahedron 1994, 50, 1539.
4. (b) Ohfune, Y. Acc. Chem. Res. 1992, 25, 360.
5. (c) Williams, R. M. Synthesis of Optically Active α-Amino Acids; Pergamon Press: Oxford, 1989.
6. For leading papers, see: (a) Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron: Asymmetry 1999, 10, 4265.
7. (b) Soloshonok, V. A.; Cai, C.; Hruby V. J.; Meervelt, L. V.; Mischenko, N. Tetrahedron 1999, 55, 12031.
8. (c) Soloshonok, V. A.; Cai, C.; Hruby, V. J.; Meervelt, L. V. Tetrahedron 1999, 55, 12045.
9. (d) Antolini, L.; Forni, A.; Moretti, I.; Prati, F. Tetrahedron: Asymmetry 1996, 7, 3309.
10. (e) Gestmann, D.; Laurent, A. J.; Laurent, E. G. J. Fluorine Chem. 1996, 80, 27.
11. (f) Hartzoulakis, B.; Gani D. J. Chem. Soc., Perkin Trans. 1 1994, 2525.
12. (g) Suzuki, K.; Seebach, D. Liebigs Ann. Chem. 1992, 51.
13. (h) Belokon, Yu. N.; Bulychev, A. G.; Pavlov, V. A.; Fedorova, E. B.; Tsyryapkin, V. A.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Perkin Trans. 1 1988, 2075.
14. (i) El Achqar, A.; Boumzebra, M.; Roumestant, M.-L.; Viallefont, P. Tetrahedron 1988, 44, 5319.
15. (j) Pettig, D.; Schöllkopf, U. Synthesis 1988, 173.
16. (k) Schöllkopf, U.; Pettig, D.; Schulze, D.; Klinge, M.; Egert, E.; Benecke, B.; Noltemeyer, M. Angew. Chem., Int. Ed. Engl. 1988, 27, 1194.
17. (l) Fitzi, R.; Seebach, D. Tetrahedron 1988, 44, 5277.
18. (m) Hartwig, W.; Born, L. J. Org. Chem. 1987, 52, 4352.
19. (n) Minowa, N.; Hirayama, M.; Fukatsu, S. Bull. Chem. Soc. Jpn. 1987, 60, 1761.
20. (o) Belokon, Yu. N.; Bulychev, A. G.; Ryznov, M. G.; Vitt, S. V.; Batsanov, A. S.; Struchkov, Yu. T.; Bakhmutov, V. I.; Belikov, V. M. J. Chem. Soc., Perkin Trans, 1 1986, 1865.
21. (p) Schöllkopf, U.; Pettig, D.; Busse, U. Synthesis 1986, 737.
22. Seebach, D.; Hoffman, M. Eur. J. Org. Chem. 1998, 1337.
23. (a) Shibuya, A.; Kurishita, M.; Ago, C.; Taguchi, T. Tetrahedron 1996, 52, 271.
24. A correction for the absolute configuration of products reported in the paper was subsequently made: (b) Shibuya, A.; Sato, A.; Taguchi, T. Bioorg. Med. Chem. Lett. 1998, 8, 1979.
25. (c) Ezquerra, J.; Pedregal, C.; Merino, I.; Flórez, J.; Barluenga, J.; Garcia-Granda, S.; Llorca, M.-A. J. Org. Chem. 1999, 64, 6554.
26. Soloshonok, V. A.; Cai, C.; Hruby, V. J. Angew. Chem., Int. Ed., in Press.
27. 9 with the phenyl on the oxazolidine ring being pointed away from the C,C double bond to exercise effective control of the face selectivity of the latter.
28. Evans, D. A. Aldrichimica Acta 1982, 15, 23.
29. Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238.
30. The corresponding mechanistic studies are currently in progress.
31. The reactions of complex 4a with more sterically demanding Michael acceptors 2, such as N-cinnamyl derivative 2e, containing a phenyl group, require even longer reaction times and thus were accompanied by formation of some byproducts.
32. 4 and evaporated in vacuo to afford a 1:1 mixture (99%) of ligand 8 and chiral auxiliary (S)-10. The aqueous solution was evaporated in vacuo, dissolved in a minimum amount of water, and loaded on cation-exchange resin Dowex 50 × 2 100. The column was washed with water, and the acidic fraction was collected to give, after evaporation in vacuo, pyroglutamic acid (2S,3S)-9a (96%). An analytically pure sample of the product was obtained by crystallization of the compound from THF/n-hexane.
33. Soloshonok, V. A.; Cai, C.; Hruby, V. J. Tetrahedron Lett. 2000, 41 (2), 135.
34. Due to the minute integral intensity of some peaks found in the NMR spectra of the crude reaction mixtures, it was impossible to conclude whether they belong to another diastereoisomers or to byproducts.
35. The (2R,3S) absolute stereochemistry for the aromatic derivatives is a consequence of the Cahn-Ingold-Prelog priorities (see ref 16) and is stereochemically equivalent to the (2R,3R) absolute configuration in the aliphatic series of compounds.
36. Cahn, R. S.; Ingold, C.; Prelog, V. Angew. Chem., Int. Ed. Engl. 1966, 5, 385.
37. Seebach, D.; Prelog, V. Angew. Chem., Int. Ed. Engl. 1982, 21, 654.