A new route to protected acyloins and their enzymatic resolution with lipases

European Journal of Organic Chemistry

Volumn , Issue 5, 2004, Pages 1063-1074

  Scheid, Günther ^a,b   Kuit, Wouter ^b   Ruijter, Eelco ^b   Orru, Romano V A ^b   Henke, Erik ^c   Bornscheuer, Uwe ^d   Wessjohann, Ludger A ^a,b  

^a LEIBNIZ INSTITUTE OF PLANT BIOCHEMISTRY   (Germany)

^b VU UNIVERSITY AMSTERDAM   (Netherlands)

^c UNIVERSITY OF STUTTGART   (Germany)

^d UNIVERSITY OF GREIFSWALD   (Germany)

Author keywords

Acyloins; Alkylation; Enzymatic catalysis; Hydrolases; Hydroxyalkanones; Kinetic resolution

Indexed keywords

ACETIC ACID DERIVATIVE; ACETOACETIC ACID DERIVATIVE; BUTYRIC ACID DERIVATIVE; CARBONYL DERIVATIVE; ENZYME; ESTER DERIVATIVE; KETONE DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ALKYLATION; ARTICLE; CARBONYLATION; CATALYSIS; ENANTIOMER; HYDROLYSIS; KINETICS; RACEMIZATION; SYNTHESIS;

EID: 4544228325     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300338     Document Type: Article

References (55)

1. R. Bel-Rhlid, A. Fauve, H. Veschambre, J. Org. Chem. 1989, 54, 3221-3223.
2. K. Awano, T. Yanai, I. Watanabe, Y. Takagi, T. Kitahara, K. Mori, Biosci. Biotechnol. Biochem. 1995, 59, 1251-1254; F. Neuser, U. Richter, R. G. Berger, Lebensmittelchem. 1999, 53, 4.
3. K. Awano, T. Yanai, I. Watanabe, Y. Takagi, T. Kitahara, K. Mori, Biosci. Biotechnol. Biochem. 1995, 59, 1251-1254; F. Neuser, U. Richter, R. G. Berger, Lebensmittelchem. 1999, 53, 4.
4. X. Shi, W. S. Leal, J. Meinwald, Bioorg. Med. Chem. 1996, 4, 297-303.
5. F. Schröder, R. Fettköther, U. Noldt, K. Dettner, W. A. König, W. Francke, Liebigs Ann. Chem. 1994, 1211-1218.
6. T. Nakata, T. Tanaka, T. Oishi, Tetrahedron Lett. 1983, 24, 2653-2656.
7. M. Larchevêque, Y. Petit, Bull. Soc. Chim. Fr. 1989, 130-139.
8. I. Paterson, D. J. Wallace, Tetrahedron Lett. 1994, 35, 9087-9090.
9. I. Paterson, D. J. Wallace, S. M. Velázquez, Tetrahedron Lett. 1994, 55, 9083-9086.
10. I. Paterson, M. D. McLeod, Tetrahedron Lett. 1995, 36, 9065-9068.
11. S. Figueras, R. Martin, P. Romea, F. Urpí, J. Vilarrasa, Tetrahedron Lett. 1991, 38, 1637-1640.
12. B. M. Trost, H. Urabe, J. Org. Chem. 1990, 55, 3982-3983.
13. H. Matsutani, S. Ichikawa, J. Yaruva, T. Kusumoto, T. Hijama, J. Am. Chem. Soc. 1997, 119, 4541.
14. C. Palomo, J. M. Aizpurua, J. M. Garcïa, R. Galarza, M. Legido, R. Urchegui, P. Román, A. Luque, Server-Carrió, A. Linden, J. Org. Chem. 1997, 62, 2070-2079.
15. C. M. Rodriguez, T. Martín, M. A. Ramírez, V. S. Martín, J. Org. Chem. 1994, 59, 4461-4472.
16. C. A. M. Afonso, M. T. Barros, L. S. Godinho, C. D. Maycock, Tetrahedron 1993, 49, 4283-4292.
17. W. Adam, F. Prechtl, Chem. Ber. 1994, 127, 667-671.
18. K. Gerlach, M. Quitschalle, M. Kalesse, Tetrahedron Lett. 1999, 40, 3553-3556.
19. P. C. B. Page, M. Purdle, D. Lathbury, Tetrahedron Lett. 1996, 37, 8929-8932.
20. C. Darcel, C. Bruneau, P. H. Dixneuf, S. M. Roberts, Tetrahedron 1997, 53, 9241-9252.
21. M. Masuda, K. Nishimura, Chem. Lett. 1981, 1333-1336.
22. O. Bortolini, G. Fantin, M. Fogagnolo, P. P. Giovannini, A. Guerrini, A. Medici, J. Org. Chem. 1997, 62, 1854-1856.
23. R. Bel-Rhlid, M. F. Renard, H. Veschambre, Bull. Soc. Chim. Fr. 1996, 133, 1011-1021.
24. L. G. Lee, G. M. Whitesides, J. Org. Chem. 1986, 51, 25-36.
25. O. Bortolini, E. Casanova, G. Fantin, A. Medici, S. Poli, S. Hanau, Tetrahedron: Asymmetry 1998, 9, 647-651.
26. M. Pohl, B. Lingen, M. Müller, Chem. Eur. J. 2002, 8, 5289-5295.
27. D. H. G. Crout, E. R. Lee, D. P. J. Pearson, J. Chem. Soc., Perkin Trans. 1 1991, 381-385.
28. Z. Guo, A. Goswami, K. D. Mirfakhrae, R. N. Patel, Tetrahedron: Asymmetry 1999, 10, 4667-4675; Z. Guo, A. Goswami, V. B. Nanduri, R. N. Patel, Tetrahedron: Asymmetry 2001, 12, 571-577.
29. Z. Guo, A. Goswami, K. D. Mirfakhrae, R. N. Patel, Tetrahedron: Asymmetry 1999, 10, 4667-4675; Z. Guo, A. Goswami, V. B. Nanduri, R. N. Patel, Tetrahedron: Asymmetry 2001, 12, 571-577.
30. [28a] W. Adam, M. T. Diaz, C. R. Saha-Möller, Tetrahedron: Asymmetry 1998, 9, 791-796.
31. [28b] K. Shioji, H. Kawaoka, A. Miura; K. Okuma, Synth. Commun. 2001, 31, 3569-3575.
32. [28c] A. S. Demir, O. Sesenoglu, Org. Lett. 2002, 4, 2021-2023.
33. T. Taniguchi, K. Ogasawara, Chem. Commun. 1997, 1399-1400.
34. T. Taniguchi, R. M. Kanada, K. Ogasawara, Tetrahedron: Asymmetry 1997, 8, 2773-2780.
35. [31a] W. Adam, M. T. Diaz, R. T. Fell, C. R. Saha-Möller, Tetrahedron: Asymmetry 1996, 7, 2207-2210.
36. [31b] H. Kajiro, S. Mitamura, A. Mori, T. Hiyama, Tetrahedron: Asymmetry 1998, 9, 907-910.
37. [32a] G Scheid, L. A. Wessjohann, Tetrahedron Lett., submitted 2004;
38. L. A. Wessjohann, G. Scheid, U. Bornscheuer, E. Henke, W. Kuit, R. V. A. Orru, Patent DE10134172A1 and W002/ 32844A2, 2002.
39. [32b] For other epothilone fragments see: U. Bornscheuer, J. Altenbuchner, H. H. Meyer, Biotechnol. Bioeng. 1998, 58, 554-559; T. Gabriel, L. Wessjohann, Tetrahedron Lett. 1997, 38, 1363-1366, and 4387-4388; L. A. Wessjohann, G. Scheid, in Organic Chemistry Highlights IV (Ed.: H.-G. Schmalz), S. 251-267, Wiley-VCH, Weinheim 2000; L. Wessjohann, Angew. Chemie, 1997, 109, 739-742, Angew. Chemie Int. Ed. Engl. 1997, 715-718.
40. [32b] For other epothilone fragments see: U. Bornscheuer, J. Altenbuchner, H. H. Meyer, Biotechnol. Bioeng. 1998, 58, 554-559; T. Gabriel, L. Wessjohann, Tetrahedron Lett. 1997, 38, 1363-1366, and 4387-4388; L. A. Wessjohann, G. Scheid, in Organic Chemistry Highlights IV (Ed.: H.-G. Schmalz), S. 251-267, Wiley-VCH, Weinheim 2000; L. Wessjohann, Angew. Chemie, 1997, 109, 739-742, Angew. Chemie Int. Ed. Engl. 1997, 715-718.
41. [32b] For other epothilone fragments see: U. Bornscheuer, J. Altenbuchner, H. H. Meyer, Biotechnol. Bioeng. 1998, 58, 554-559; T. Gabriel, L. Wessjohann, Tetrahedron Lett. 1997, 38, 1363-1366, and 4387-4388; L. A. Wessjohann, G. Scheid, in Organic Chemistry Highlights IV (Ed.: H.-G. Schmalz), S. 251-267, Wiley-VCH, Weinheim 2000; L. Wessjohann, Angew. Chemie, 1997, 109, 739-742, Angew. Chemie Int. Ed. Engl. 1997, 715-718.
42. [32b] For other epothilone fragments see: U. Bornscheuer, J. Altenbuchner, H. H. Meyer, Biotechnol. Bioeng. 1998, 58, 554-559; T. Gabriel, L. Wessjohann, Tetrahedron Lett. 1997, 38, 1363-1366, and 4387-4388; L. A. Wessjohann, G. Scheid, in Organic Chemistry Highlights IV (Ed.: H.-G. Schmalz), S. 251-267, Wiley-VCH, Weinheim 2000; L. Wessjohann, Angew. Chemie, 1997, 109, 739-742, Angew. Chemie Int. Ed. Engl. 1997, 715-718.
43. [32b] For other epothilone fragments see: U. Bornscheuer, J. Altenbuchner, H. H. Meyer, Biotechnol. Bioeng. 1998, 58, 554-559; T. Gabriel, L. Wessjohann, Tetrahedron Lett. 1997, 38, 1363-1366, and 4387-4388; L. A. Wessjohann, G. Scheid, in Organic Chemistry Highlights IV (Ed.: H.-G. Schmalz), S. 251-267, Wiley-VCH, Weinheim 2000; L. Wessjohann, Angew. Chemie, 1997, 109, 739-742, Angew. Chemie Int. Ed. Engl. 1997, 715-718.
44. S.-O. Lawesson, S. Grönwall, Acta Chem. Scand., Ser. A 1960, 14, 1445-1446.
45. J.-F. Lavallée, R. Rej, M. Courchesne, D. Nguyen, G. Attardo, Tetrahedron Lett. 1993, 34, 3519-3522.
46. A. P. Krapcho, G. Gadamasetti, J. Org. Chem. 1987, 52, 1880-1881.
47. J. L. L. Rakels, A. J. J. Straathof, J. J. Heijnen, Enz. Microb. Technol. 1993, 15, 1051-1056.
48. C.-S. F. Chen, G. Girdaukas, C. J. Sih, J. Am. Chem. Soc. 1982, 104, 7294-7299.
49. [38a] R. J. Kazlauskas, A. N. E. Weissfloch, A. T. Rappaport, L. A. Cuccia, J. Org. Chem. 1991, 56, 2656-2665.
50. [38b] U. Th. Bornscheuer, R. J. Kazlauskas, in Hydrolases in Organic Synthesis, Wiley-VCH, Weinheim, 1999.
51. U. T. Strauss, K. Faber, Tetrahedron: Asymmetry 1999, 10, 4079-4081.
52. [40a] M. Masuda, K. Nishimura, Chem. Lett. 1981, 1333-1336.
53. [40b] K. Awano, T. Yanai, I. Watanabe, Y. Takagi, T. Kitahara, K. Mori, Biosci. Biotechnol. Biochem. 1995, 59, 1251-1254.
54. [40c] S. K. Latypov, J. M. Seco, E. Quiñoá, R. Riguera, J. Am. Chem. Soc. 1998, 120, 877-882.
55. Derivatisation of 6g and 61 as (R)-MPA esters according to Latypov [40c] produced a somewhat diminished der, In the case of 6g this was due to relatively high spontaneous hydrolysis (ca. 4.3% within 30 min). For 61 the E value was rather low, resulting in a diastereomeric mixture of (R)-MTPA esters. However, it was still possible to assign the absolute configuration.