Preparation and asymmetric hydrogenation of β-aryl-substituted β-acylaminoacrylates

Angewandte Chemie - International Edition

Volumn 42, Issue 8, 2003, Pages 913-916

  You, Jingsong ^a   Drexler, Hans Joachim ^a   Zhang, Songlin ^a   Fischer, Christine ^a   Heller, Detlef ^a  

^a UNIVERSITY OF ROSTOCK   (Germany)

Author keywords

Amino acids; Asymmetric catalysis; Hydrogenation; P ligands; Rhodium

Indexed keywords

CATALYSIS; HYDROGENATION; RHODIUM; SUBSTRATES; SYNTHESIS (CHEMICAL);

ASYMMETRIC HYDROGENATION;

ORGANIC COMPOUNDS;

1,1' BIS(2,4 DIETHYLPHOSPHYLTANE)FERROCENE; ACRYLIC ACID DERIVATIVE; FERROCENE DERIVATIVE; LIGAND; METHYL 3 DIACETYLAMINO 3 PHENYLACRYLATE; RHODIUM; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHIRALITY; ENANTIOSELECTIVITY; HYDROGENATION; ISOMER; PRESSURE; STRUCTURE ANALYSIS; SYNTHESIS; TEMPERATURE;

EID: 0037463057     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200390242     Document Type: Article

References (36)

1. a) E. Juaristi, H. Lopez-Ruiz, Curr. Med. Chem. 1999, 6, 983-1004;
2. b) Enantioselective synthesis of β-amino acids (Ed.: E. Juaristi), Wiley-VCH, Weinheim, 1997;
3. c) G. Cardillo, C. Tomasini, Chem. Soc. Rev. 1996, 25, 117-128;
4. d) D.C. Cole, Tetrahedron 1994, 50, 9517-9582.
5. a) D. Heller, H.-J. Drexler, J. You, W. Baumann, K. Drauz, H.-P. Krimmer, A. Börner, Chem. Eur. J. 2002, 8. 5196-5203;
6. b) S. Lee, Y. J. Zhang, Org. Lett. 2002, 4, 2429-2431;
7. c) Y. G. Zhou, W. Tang, W.-B. Wang, W. Li, X. Zhang, J. Am. Chem. Soc. 2002, 124, 4952-4953;
8. d) D. Heller, H.-J. Drexler, A. Spannenberg, B. Heller, J. You, W. Baumann, Angew. Chem. 2002, 114, 814-817; Angew. Chem. Int. Ed. 2002, 41, 777-780;
9. D. Heller, H.-J. Drexler, A. Spannenberg, B. Heller, J. You, W. Baumann, Angew. Chem. 2002, 114, 814-817; Angew. Chem. Int. Ed. 2002, 41, 777-780;
10. e) D. Heller, J. Holz, H.-J. Drexler, J. Lang, K. Drauz, H.-P. Krimmer, A. Börner, J. Org. Chem. 2001, 66, 6816-6817;
11. f) M. Yasutake, I. D. Gridnev, N. Higashi, T. Imamoto, Org. Lett. 2001, 3, 1701-1704;
12. g) G. Zhu, Z. Chen, X. Zhang, J. Org. Chem. 1999, 64, 6907-6910;
13. h) W.D. Lubell, M. Kitamura, R. Noyori, Tetrahedron: Asymmetry. 1991, 2, 543-554;
14. i) K. Achiwa, T. Soga, Tetrahedron Lett. 1978, 1119-1120;
15. j) B. D. Vineyard, W. S. Knowles, M. J. Sabacky, G. L. Bachmann, D. J. Weinkauff, J. Am. Chem. Soc. 1977, 99, 5946-5952.
16. Full characterization and X-ray structural analysis of this compound, which is reported for the first time, are found in the Supporting Information.
17. [13l leads to the hydrogenation of the Z isomer only, the "E isomer" remains unchanged. Unlike the starting materials, which are difficult to separate, the hydrogenation product is readily separated from the unchanged "E isomer" by column chromatography when the latter is obtained in a pure state.
18. 4) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www:ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam.ac.uk).
19. Compare similar findings on the preparation of analogous but β-alkyl-substituted substrates: a) D. J. Aberhardt, H.-J. Lin, J. Org. Chem. 1981, 46, 3749-3751; b) P. deMayo, A. C. Weedon, R. W. Zabel, Can. J. Chem. 1981, 59, 2328-2333 c) C. A. Grob, Helv. Chim. Acta 1950, 33, 1787-1796.
20. Compare similar findings on the preparation of analogous but β-alkyl-substituted substrates: a) D. J. Aberhardt, H.-J. Lin, J. Org. Chem. 1981, 46, 3749-3751; b) P. deMayo, A. C. Weedon, R. W. Zabel, Can. J. Chem. 1981, 59, 2328-2333 c) C. A. Grob, Helv. Chim. Acta 1950, 33, 1787-1796.
21. Compare similar findings on the preparation of analogous but β-alkyl-substituted substrates: a) D. J. Aberhardt, H.-J. Lin, J. Org. Chem. 1981, 46, 3749-3751; b) P. deMayo, A. C. Weedon, R. W. Zabel, Can. J. Chem. 1981, 59, 2328-2333 c) C. A. Grob, Helv. Chim. Acta 1950, 33, 1787-1796.
22. a) H.-J. Drexler, W. Baumann, A. Spannenberg, D. Heller, J. Organomet. Chem. 2001, 621, 89-102;
23. b) A. Börner, D. Heller, Tetrahedron Lett. 2001, 42, 223-225;
24. c) C. J. Cobley, I. C. Lennon, R. McCague, J. A. Ramsden, A. Zanotti-Gerosa, Tetrahedron Lett. 2001, 42, 7481-7483.
25. a) H. B. Kagan, T.-P. Dang, J. Am. Chem. Soc. 1972, 94, 6429-6433;
26. b) W. S. Knowles, M. J. Sabacky, B. D. Vineyard, D. J. Weinkauff, J. Am. Chem. Soc. 1975, 97, 2567-2568;
27. c) M. J. Burk, J. Am. Chem. Soc. 1991, 113, 8518-8519;
28. d) M. J. Burk. J. E. Feaster, W. A. Nugent, R. L. Harlow, J. Am. Chem. Soc. 1993, 115, 10125-10138;
29. e) A. Marinetti, F. Labrue, J.-P. Genet, Synlett 1999, 12, 1975-1977;
30. f) U. Berens, M. J. Burk, A. Gerlach, W. Hems, Angew. Chem. 2000, 112, 2057-2060; Angew. Chem. Int. Ed. 2000, 39, 1981-1984.
31. f) U. Berens, M. J. Burk, A. Gerlach, W. Hems, Angew. Chem. 2000, 112, 2057-2060; Angew. Chem. Int. Ed. 2000, 39, 1981-1984.
32. The hydrogenation of the corresponding Z isomers with the Et-FerroTANE system leads, as expected, to enantioselectivities of only 25-80% ee. Orienting investigations with Me-DuPHOS with the E isomers as substrates gave throughout poorer enantioselectivities and activities.
33. In the case of the p-chlorophenyl-substituted product the determination of the absolute S configuration was achieved by X-ray structure analysis (see Supporting Information). Since all other hydrogenation products also gave negative rotations they should equally be S-configurated, which is in agreement with literature data.
34. P. Dierkes, P. W. N. M. van Leeuwen, J. Chem. Soc. Dalton Trans. 1999, 1519-1529.
35. B. Guzel, M. A. Omary, J. P. Fackler, A. Akgerman, Inorg. Chim. Acta 2001, 325, 45-50.
36. Abreviations used: binapo=2,2′-Bis(diphenylphosphanyl)-1,1′- binaphthyl, dipamp = 1,2-ethanediylbis[(2-methoxyphenyl)phenylphosphane], diop = 2,3-O-isopropylidene-2,3-dihydroxy-1,4- bis(diphenylphosphanyl)butane, Me-DuPHOS = 1,2-bis(2,5-di- methylphospholanyl)benzene, Et-FerroTANE = 1,1′-bis(2,4-di-ethylphosphetanyl)ferrocene, nbd = 3,5-norbornadiene, cod = 1,5-cyclooctadiene.