Synthesis of (+)-(R)-1-Amino-2,2-difluorocyclopropane-1-carboxylic acid through lipase-catalyzed asymmetric acetylation

Chemistry Letters

Volumn , Issue 5, 1999, Pages 405-406

  Kirihara, Masayuki ^a   Takuwa, Tomofumi ^a   Kawasaki, Masashi ^b   Kakuda, Hiroko ^a   Hirokami, Shun Ichi ^a   Takahata, Hiroki ^a  

^a UNIVERSITY OF TOYAMA   (Japan)

^b TOYAMA PREFECTURAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033241994     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.405     Document Type: Article

References (19)

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2. L. F. Burroughs, Nature, 179, 360 (1957); D. O. Adams and S. F. Yang, Proc. Natl. Acad. Sci. U. S. A., 76, 170 (1979); J-C. G. Marvizón, A. H. Lewin, and P. Skolnick, J. Neurochem., 52, 992 (1989); V. Nadler, Y. Kloog, and M. Sokolovsky, Eur. J. Pharmacol., 157, 115 (1988); D.K.J.E, Von Lubitz, R. C.-S. Lin, R. J. McKenzie, T.M. Devlin, R. T. McCabe, and P. Skolnick, Eur. J. Pharmacol., 219, 153 (1992); H. Kodama and Y. Shimohigashi, J. Synth. Org. Chem. Jpn., 52, 180 (1994).
3. L. F. Burroughs, Nature, 179, 360 (1957); D. O. Adams and S. F. Yang, Proc. Natl. Acad. Sci. U. S. A., 76, 170 (1979); J-C. G. Marvizón, A. H. Lewin, and P. Skolnick, J. Neurochem., 52, 992 (1989); V. Nadler, Y. Kloog, and M. Sokolovsky, Eur. J. Pharmacol., 157, 115 (1988); D.K.J.E, Von Lubitz, R. C.-S. Lin, R. J. McKenzie, T.M. Devlin, R. T. McCabe, and P. Skolnick, Eur. J. Pharmacol., 219, 153 (1992); H. Kodama and Y. Shimohigashi, J. Synth. Org. Chem. Jpn., 52, 180 (1994).
4. L. F. Burroughs, Nature, 179, 360 (1957); D. O. Adams and S. F. Yang, Proc. Natl. Acad. Sci. U. S. A., 76, 170 (1979); J-C. G. Marvizón, A. H. Lewin, and P. Skolnick, J. Neurochem., 52, 992 (1989); V. Nadler, Y. Kloog, and M. Sokolovsky, Eur. J. Pharmacol., 157, 115 (1988); D.K.J.E, Von Lubitz, R. C.-S. Lin, R. J. McKenzie, T.M. Devlin, R. T. McCabe, and P. Skolnick, Eur. J. Pharmacol., 219, 153 (1992); H. Kodama and Y. Shimohigashi, J. Synth. Org. Chem. Jpn., 52, 180 (1994).
5. L. F. Burroughs, Nature, 179, 360 (1957); D. O. Adams and S. F. Yang, Proc. Natl. Acad. Sci. U. S. A., 76, 170 (1979); J-C. G. Marvizón, A. H. Lewin, and P. Skolnick, J. Neurochem., 52, 992 (1989); V. Nadler, Y. Kloog, and M. Sokolovsky, Eur. J. Pharmacol., 157, 115 (1988); D.K.J.E, Von Lubitz, R. C.-S. Lin, R. J. McKenzie, T.M. Devlin, R. T. McCabe, and P. Skolnick, Eur. J. Pharmacol., 219, 153 (1992); H. Kodama and Y. Shimohigashi, J. Synth. Org. Chem. Jpn., 52, 180 (1994).
6. L. F. Burroughs, Nature, 179, 360 (1957); D. O. Adams and S. F. Yang, Proc. Natl. Acad. Sci. U. S. A., 76, 170 (1979); J-C. G. Marvizón, A. H. Lewin, and P. Skolnick, J. Neurochem., 52, 992 (1989); V. Nadler, Y. Kloog, and M. Sokolovsky, Eur. J. Pharmacol., 157, 115 (1988); D.K.J.E, Von Lubitz, R. C.-S. Lin, R. J. McKenzie, T.M. Devlin, R. T. McCabe, and P. Skolnick, Eur. J. Pharmacol., 219, 153 (1992); H. Kodama and Y. Shimohigashi, J. Synth. Org. Chem. Jpn., 52, 180 (1994).
7. M. J. Sloan and K. L. Kirk, Tetrahedron Lett., 38, 1677 (1997).
8. Taguchi and co-workers recently reported the synthesis of amino acids containing the difluorocyclopropane moiety [2-(2-carboxy-3,3-difluorocyclopropyl)glycines]; A. Shibuya, A. Sato, and T. Taguchi, Bioorg. Med. Chem. Lett., 8, 1979 (1998).
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11. Itoh and co-workers recently reported the lipase-catalyzed asymmetric hydrolysis of cis-1,2-bis(acetoxymethyl)-3,3-difluorocyclopropane; T. Itoh, K. Mitsukura, and M. Furutani, Chem. Lett., 1998, 903.
12. C. R. Wescott and A. M. Klibanov, Biochim. Biophys. Acta, 1206, 1 (1994).
13. These compounds were purified by recrystallization from n-hexane (for 8b and 9b) or n-hexane / ethyl acetate (for 8a and 9a).
14. K. Ninomiya, T. Shioiri, and S. Yamada, Tetrahedron, 30, 2151 (1974).
15. Based on HPLC analysis of the benzoyl esters of 9. The optical purity of these compounds turned out to be almost 100%ee. Only one enantiomer was detected.
16. -1, 2801 reflections measured, 2657 reflections unique, R1 = 0.0572, wR2 = 0.1703.
17. The enantiopreference of the lipase-catalyzed asymmetric acetylation of 5 followed the empirical rule proposed by Kazlauskas et al.: A. N. E. Weissfloch and R. J. Kazlauskas, J. Org. Chem., 60, 6959 (1995).
18. 3CN or aq.KOH-MeOH) to deprotect the Cbz group from 11a were unsuccessful.
19. ++H) 138.0367.