Synthesis and use of α-silyl-substituted α-hydroxyacetic acids

Organic Letters

Volumn 4, Issue 13, 2002, Pages 2265-2267

  Bolm, Carsten ^a   Kasyan, Andrey ^a   Heider, Peter ^a   Saladin, Sandra ^a   Drauz, Karlheinz ^b   Günther, Kurt ^c   Wagner, Christoph ^d  

^a RWTH AACHEN UNIVERSITY   (Germany)

^b EVONIK INDUSTRIES AG   (Germany)

^c Infracor GmbH   (Germany)

^d MARTIN LUTHER UNIVERSITY HALLE WITTENBERG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BIOLOGICAL FACTOR; GLYCOLIC ACID; GLYCOLIC ACID DERIVATIVE; LIGAND; SILANE DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

BIOLOGICAL FACTORS; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; GLYCOLATES; LIGANDS; MOLECULAR STRUCTURE; SILANES;

EID: 0037182717     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol025911n     Document Type: Article

References (45)

1. (a) Scott, J. W. In Asymmetric Synthesis; Morrison, J. D., Scott, J. W., Eds.; Academic Press: New York, 1984; Vol. 4, p 1.
2. (b) Seebach, D.; Hungerbühler, E. In Modern Synthetic Methods; Scheffold, R., Ed.; Otto Salle Verlag: Frankfurt, 1980; Vol. 2, p 91.
3. (c) Coppola, G. M.; Schuster, H. F. Hydroxy Acids In Enantioselective Synthesis; Wiley-VCH: Weinheim, 1997.
4. (a) Pearson, W. H.; Cheng, M.-C. J. Org. Chem. 1986, 51, 3746.
5. (b) Seebach, D.; Naef, R.; Calderari, G. Tetrahedron 1984, 40, 1313.
6. (c) Ley, S. V.; Boons, G.-J.; Downham, R.; Kim, K. S.; Woods, M. Tetrahedron 1994, 50, 7157.
7. (d) Xiang, Y. B.; Snow, K.; Belley, M. J. Org. Chem. 1993, 58, 993.
8. (e) Camps, P.; Perez, F.; Soldevilla, N. Tetrahedron: Asymmetry 1997, 8, 1877.
9. (f) Wang, Z.; La, B.; Fortunak, J. M.; Meng, X.-J.; Kabalka, G. W. Tetrahedron Lett. 1998, 39, 5501.
10. (g) Cavelier, F.; Gomez, S.; Jacquier, R.; Verducci, J. Tetrahedron Lett. 1994, 35, 2891.
11. (h) Adam, W.; Fell, R. T.; Stegmann, V. R.; Saha-Möller, C. R. J. Am. Chem. Soc. 1998, 120, 708.
12. (i) Yamamoto, Y.; Kin, H.; Suzuki, I.; Asao, N. Tetrahedron Lett. 1996, 37, 1863.
13. (j) Kirschning, A.; Dräger, G.; Jung, A. Angew. Chem. 1997, 109, 253; Angew. Chem., Int. Ed. Engl. 1997, 36, 253.
14. (j) Kirschning, A.; Dräger, G.; Jung, A. Angew. Chem. 1997, 109, 253; Angew. Chem., Int. Ed. Engl. 1997, 36, 253.
15. (k) Chang, J.-W.; Jang, D.-P.; Uang, B.-J.; Liao, F.-L.; Wang, S.-L. Org. Lett. 1999, 1, 2061.
16. To the best of our knowledge, only one other compound of this class has been reported before. However, in contrast to our work, this derivative had a quartenary α-carbon bearing an additional methyl group at C2, and it was obtained via an entirely different synthetic route (alkyne oxidation). Murray, R. W.; Singh, M.; Rath, N. P. Acta Crystallogr., Sect. C 1996, 52, 1282.
17. (a) Schank, K.; Beck, H.; Werner, F. Helv. Chim. Acta 2000, 83, 1611.
18. (b) Sekiguchi, A.; Ando, W. J. Chem. Soc., Chem. Commun. 1979, 575.
19. (a) Thorsett, E. D. Tetrahedron Lett. 1982, 23, 1875.
20. (b) Garcia, F. S.; Cebrián, G. M. P.; Löpez, A. H.; Herrara, F. J. L. Tetrahedron 1998, 54, 6867.
21. (a) Darkins, P.; McCarthy, N.; McKervey, M. A.; O'Donnell, K.; Ye, T.; Walker, B. Tetrahedron: Asymmetry 1994, 5. 195.
22. (b) Saba, A. Synth. Commun. 1994, 24, 695.
23. (a) Sekiguchi, A.; Kabe, Y.; Ando, W. Tetrahedron Lett. 1979, 871.
24. (b) Sekiguchi, A.; Kabe, Y.; Ando, W. J. Org. Chem. 1982, 47, 2900.
25. (a) Martin. M. G.; Ganem. B. Tetrahedron Lett. 1984, 25, 251.
26. (b) McKenna, C. E.; Levy, J. N. J. Chem. Soc., Chem. Commun. 1989, 246.
27. (c) Solbakken, M.; Skramstad, J. Acta Chem. Scand. 1993, 47, 1214.
28. (a) For the synthesis of 3 from benzyl 2-diazoacetates with triorgaδ nylsilyltriflates, see: Bolm, C.; Kasyan, A.; Drauz, K.; Günther, K.; Raabe, G. Angew. Chem. 2000, 112, 2374; Angew. Chem. Int. Ed. 2000, 39, 2288.
29. (a) For the synthesis of 3 from benzyl 2-diazoacetates with triorgaδ nylsilyltriflates, see: Bolm, C.; Kasyan, A.; Drauz, K.; Günther, K.; Raabe, G. Angew. Chem. 2000, 112, 2374; Angew. Chem. Int. Ed. 2000, 39, 2288.
30. (b) The synthesis of the required triorganylsilyltriflates was accomplished according to: Uhlig, W. Chem. Ber. 1992, 125, 43.
31. (a) For an analogous reactivity, see: Maas, G.; Bender, S. Chem. Commun. 2000, 437.
32. (b) An excellent overview of silyl-substituted carbenes may be found in: Maas, G. In The Chemistry of Organic Silicon Compounds: Rappoport, Z., Apeloig, Y., Eds.; Wiley: Chichester, 1998; Vol. 2, Part 1, Chapter 13, p 703.
33. Hilbert, J. M.; Fedor, L. J. Org. Chem. 1978, 43, 452.
34. The crystallographic data for the compound (rac-1c) was deposited as Supporting Information at the Cambridge Crystallographic Data Centre under the publication no. CCDC-174123. Copies may be obtained free of charge from the following location in Great Britain: CCDC, 12 Union Road, Cambridge CB2 1EZ (FAX: (+44) 1223-336-033. E-mail: deposit@ ccdc.cam.ac.uk).
35. F. H. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, S1.
36. R (+)-6a: 25.3 min. Preparative: as for analytic separation but using 40 mm x 250 mm, 225 nm, and 40 mL/min
37. 12
38. 14 The (+)-enantiomer of 6a was hydrogenolytically debenzylated to the hydroxyacetic acid (+)-1a (76% yield) by means of Pd/C catalysis.
39. For current overviews of this field, see: (a) Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357.
40. (b) Carreira, E. M. In Comprehensive Asymmetric Catalysis; Jacobsen, E. N., A. Pfaltz, A., H. Yamamoto, H., Eds.; Springer: Berlin, 1999; Vol. 3, p 998.
41. CAB stands for "chiral acyloxyborane" and describes catalysts that are synthesized from boranes with chiral carboxylic acids (i.e., α-hydroxy-and α-amino acids). For examples, see: (a) Takasu, M.; Yamamoto, H. Synlett 1990, 194.
42. (b) Sartor, D.; Saffrich, J.; Helmchen, G. Synlett 1990, 197.
43. Ishihara, K.; Kondo, S.; Yamamoto, H. J. Org. Chem. 2000, 65, 9125 and references therein.
44. R (S)-9 35 min (major).
45. Recently, it has been shown that α-hydroxyacids with bulky substituents may be successfully used as chiral ligands in the enantioselective addition of diethylzinc to benzaldehyde, achieving good ee's. Bauer, T.; Tarasiuk, J. Tetrahedron Lett. 2002, 43, 687.