Lipase-catalyzed kinetic resolution of cyclic trans-1,2-diols bearing a diester moiety: Synthetic application to chiral seven-membered-ring α,α-disubstituted α-amino acid

Journal of Organic Chemistry

Volumn 72, Issue 20, 2007, Pages 7750-7756

  Tanaka, Masakazu ^a   Demizu, Yosuke ^a,c   Nagano, Masanobu ^a   Hama, Mariko ^a   Yoshida, Yukio ^a   Kurihara, Masaaki ^b   Suemune, Hiroshi ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b NATIONAL INSTITUTE OF HEALTH SCIENCES   (Japan)

^c NAGASAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACIDS; CATALYSIS; CHIRALITY; ENZYME KINETICS; EPOXIDATION; HYDROLYSIS; OLEFINS;

DIESTER MOIETY; DIOLS; KINETIC RESOLUTION; OLEFIN METATHESIS;

ALCOHOLS;

ACETIC ACID DERIVATIVE; ALKENE; ALKENYL GROUP; ALPHA AMINO ACID; CYCLOALKANE; CYCLOPENTANE; GLYCOL; MALONIC ACID; TRIACYLGLYCEROL LIPASE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; COMPLEX FORMATION; ENANTIOMER; ENZYME SUBSTRATE; ENZYME SUBSTRATE COMPLEX; EPOXIDATION; QUANTUM YIELD; RACEMIC MIXTURE; REACTION ANALYSIS; SYNTHESIS; TRANSESTERIFICATION;

ALCOHOLS; AMINO ACIDS, CYCLIC; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; CYCLOHEPTANES; CYCLOPENTANES; ESTERS; KINETICS; LIPASE; MODELS, MOLECULAR; STEREOISOMERISM;

EID: 34848817361     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo701317d     Document Type: Article

References (40)

1. Bhowmick, K. C.; Joshi, N. N. Tetrahedron; Asymmetry 2006, 17, 1901-1929 and references cited therein.
2. Chiral cyclic 1,2-diols and their application to asymmetric reactions by us. See: (a) Sakai, K.; Suemune, H. Tetrahedron: Asymmetry 1993, 4, 2109-2118.
3. (b) Kiguchi, T.; Tsurusaki, Y.; Yamada, S.; Aso, M.; Tanaka, M.; Sakai, K.; Suemune, H. Chem. Pharm. Bull. 2000, 48, 1536-1540.
4. (c) Tanaka, M.; Toyofuku, E.; Demizu, Y.; Yoshida, O.; Nakazawa, K.; Sakai, K.; Suemune, H. Tetrahedron 2004, 60, 2271-2281.
5. (d) Suemune, H.; Aso, M. J. Synth. Org. Chem., Jpn. 2005, 63, 807-814.
6. Lipase-catalyzed kinetic resolution of cyclic 1,2-diols. See: (a) Xie, Z. F.; Nakamura, I.; Suemune, H.; Sakai, K. J. Chem. Soc., Chem. Commun. 1988, 966-967.
7. (b) Seemayer, R.; Schneider, M. P. J. Chem. Soc., Chem. Commun. 1991, 49-50.
8. (c) Kazlauskas, R. J.; Weissfloch, A. N. E.; Rappaport, A. T.; Cuccia, L. A. J. Org. Chem. 1991, 56, 2656-2665.
9. (d) Caron, G.; Kazlauskas, R. J. J. Org. Chem. 1991, 56, 7251-7256.
10. (e) Naemura, K.; Fukuda, R.; Kurata, M.; Konishi, M.; Hirose, K.; Tobe, Y. Tetrahedron: Asymmetry 1995, 6, 2385-2394.
11. (a) Tanaka, M. J. Synth. Org. Chem., Jpn. 2002, 60, 125-136.
12. (b) Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 1998, 9, 3517-3599.
13. (c) Cativiela, C.; Diaz-de-Villegas, M. D. Tetrahedron: Asymmetry 2000, 11, 645-732.
14. (d) Vogt, H.; Bräse, S. Org. Biomol. Chem. 2007, 5, 406-430 and references cited therein.
15. (a) Tanaka, M.; Demizu, Y.; Doi, M.; Kurihara, M.; Suemune, H. Angew. Chem., Int. Ed. 2004, 43, 5360-5363.
16. (b) Tanaka, M.; Anan, K.; Demizu, Y.; Kurihara, M.; Doi, M.; Suemune, H. J. Am. Chem. Soc. 2005, 127, 11570-11571.
17. (c) Tanaka, M. Yakugaku Zasshi 2006, 126, 931-944.
18. (d) Tanaka, M. Chem. Pharm. Bull. 2007, 55, 349-3-58.
19. Tanaka, M.; Oba, M.; Tamai, K.; Suemune, H. J. Org. Chem. 2001, 66, 2667-2673.
20. Part of this work has already been presented in the Japanese Peptide Symposium. See: Hama, M.; Tanaka, M.; Yoshida, Y.; Demizu, Y.; Kurihara, M.; Suemune, H. Peptide Science 2006; Proceedings of the International Conference of the 43rd Japanese Peptide Symposium and 4th Peptide Engineering Meeting; Japanese Peptide Society: Minoh, Osaka, Japan, 2006; pp 39-40.
21. Fürstner, A.; Hill, A. F.; Liebl, M.; Wilton-Ely, J. D. E. T. Chem. Commun. 1999, 601-602.
22. Recent publications of lipase-catalyzed kinetic resolution of racemic alcohols. For example, see: (a) Ema, T.; Fujii, T.; Ozaki, M.; Korenaga, T.; Sakai, T. Chem. Commun. 2005, 4650-4651.
23. (b) Akita, H.; Takano, Y.; Nedu, K.; Kato, K. Tetrahedron: Asymmetry 2006, 17, 1705-1714.
24. (c) Akai, S.; Tanimoto, K.; Kanao, Y.; Egi, M.; Yamamoto, T.; Kita, Y. Angew. Chem., Int. Ed. 2006, 45, 2592-2595 and references cited therein.
25. Amano PS is a Burkholderia cepacia lipase, which was formerly used as Pseudomonas fluorescens lipase (PFL) or P. cepacia lipase, and Amano AK is now classified as Pseudomonas fluorescens lipase.
26. (a) Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; John Wiley & Sons, Inc.: New York, 1996; pp 1043-1050.
27. (b) Nakanishi, K.; Berova, N.; Woody, R. W., Eds. Circular Dichroism: Principles and Applications; VCH: New York, 1994.
28. Synthesis of (S,S)-13 from dimethyl L-(+)-tartrate has already been presented. See: Demizu, Y.; Tanaka, M.; Kurihara, M.; Suemune, H. Peptide Science 2002; Proceedings of the 39th Japanese Peptide Symposium; Japanese Peptide Society: Minoh, Osaka, Japan, 2003; pp 321-322.
29. (a) Kim, K. K.; Song, H. K.; Shin, D. H.; Hwang, K. Y.; Suh, S. W. Structure 1997, 5, 173-185.
30. (b) Schrag, J. D.; Li, Y.; Cygler, M.; Lang, D.; Burgdorf, T.; Hecht, H.-J.; Schmid, R.; Schomburg, D.; Rydel, T. J.; Oliver, J. D.; Strickland, L. C.; Dunaway, C. M.; Larson, S. B.; Day, J.; McPherson, A. Structure 1997, 5, 187-202.
31. (c) Luić, M.; Tomić, S.; Leščić, I.; Ljubović, E.; Šepac, D.; Šunjić, V.; Vitale, L.; Saenger, W.; Kojić-Prodić, B. J. Biochem. 2001, 268, 3964-3973.
32. (d) Mezzetti, A.; Schrag, J. D.; Cheong, C. S.; Kazlauskas, R. J. Chem. Biol. 2005, 12, 427-437.
33. (a) Schulz, T.; Pleiss, J.; Schmid, R. D. Protein Sci. 2000, 9, 1053-1062.
34. (b) Tafi, A. T.; van-Almsick, A.; Corelli, F.; Crusco, M.; Laumen, K. E.; Schneider, M. P.; Botta, M. J. Org. Chem. 2000, 65, 3659-3665.
35. Tuomi, W. V.; Kazlauskas, R. J. J. Org. Chem. 1999, 64, 2638-2647.
36. (a) Shioiri, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc. 1972, 94, 6203-6205.
37. (b) Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron 1974, 30, 2151-2157.
38. (c) Evans, D. A.; Wu, L. D.; Wiener, J. J. M.; Johnson, J. S.; Ripin, D. H. B.; Tedrow, J. S. J. Org. Chem. 1999, 64, 6411-6417.
39. (d) Ghosh, A. K.; Fidanze, S. J. Org. Chem. 1998, 63, 6146-6152.
40. (e) Spino, C.; Godbout, C. J. Am. Chem. Soc. 2003, 125, 12106-12107.