Dynamic kinetic resolution of 1,3-dihydro-2 h-isoindole-1-carboxylic acid methyl ester: Asymmetric transformations toward isoindoline carbamates

Organic Letters

Volumn 14, Issue 7, 2012, Pages 1696-1699

  Morán Ramallal, Roberto ^a   Gotor Fernández, Vicente ^a   Laborda, Pedro ^b   Sayago, Francisco J ^b   Cativiela, Carlos ^b   Gotor, Vicente ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

^b UNIVERSITY OF ZARAGOZA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAMIC ACID DERIVATIVE; CARBOXYLIC ACID; ISOINDOLE DERIVATIVE; TRIACYLGLYCEROL LIPASE;

ARTICLE; BURKHOLDERIA CEPACIA; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; ENZYMOLOGY; KINETICS; METABOLISM; STEREOISOMERISM; SYNTHESIS;

BURKHOLDERIA CEPACIA; CARBAMATES; CARBOXYLIC ACIDS; CATALYSIS; ISOINDOLES; KINETICS; LIPASE; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 84859569055     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol300250h     Document Type: Article

References (33)

1. Bare, T. M.; Draper, C. W.; McLaren, C. D.; Pullan, L. M.; Patel, J.; Patel, P. B. Bioorg. Med. Chem. Lett. 1993, 3, 55
2. Kukkola, P. J.; Bilci, N. A.; Ikler, T.; Savage, P.; Shetty, S. S.; DelGrande, D.; Jeng, A. Y. Bioorg. Med. Chem. Lett. 2001, 11, 1737
3. Van Goethem, S.; Van der Veken, P.; Dubois, V.; Soroka, A.; Lambeir, A.-M.; Chen, X.; Haemers, A.; Scharpé, S.; De Meester, I.; Agustyns, K. Bioorg. Med. Chem. Lett. 2008, 18, 4159
4. Cignarella, G.; Sanna, P. J. Med. Chem. 1981, 24, 1003
5. Klutchko, S.; Blankley, C. J.; Fleming, R. W.; Hinkley, J. M.; Werner, A. E.; Nordin, I.; Holmes, A.; Hoefle, M. L.; Cohen, D. M.; Essenburg, A. D.; Kaplan, H. R. J. Med. Chem. 1986, 29, 1953
6. Chiba, J.; Takayama, G.; Takashi, T.; Yokoyama, M.; Nakayama, A.; Baldwin, J. J.; McDonald, E.; Moriarty, K. J.; Sarko, C. R.; Saionz, K. W.; Swanson, R.; Hussain, Z.; Wong, A.; Machinaga, N. Bioorg. Med. Chem. 2006, 14, 2725
7. Kung, P.-P.; Huang, B.; Zhang, G.; Zhou, J. Z.; Wang, J.; Digits, J. A.; Skaptason, J.; Yamazaki, S.; Neul, D.; Zientek, M.; Elleraas, J.; Mehta, P.; Yin, M.-J.; Hickey, M. J.; Gajiwala, K. S.; Rodgers, C.; Davies, J. F., II; Gehring, M. R. J. Med. Chem. 2010, 53, 499
8. Reddy, M. V. N.; Krishna, A. B.; Reddy, C. S. Eur. J. Med. Chem. 2010, 45, 1828
9. Luckhurst, C. A.; Stein, L. A.; Furber, M.; Webb, N.; Ratcliffe, M. J.; Allenby, G.; Botterell, S.; Tomlinson, W.; Martin, B.; Walding, A. Bioorg. Med. Chem. Lett. 2011, 21, 492
10. Cignarella, G.; Cerri, R.; Grella, G.; Sanna, P. Gazz. Chim. Ital. 1976, 106, 65
11. New, J. S.; Yevich, J. P. J. Heterocyclic Chem. 1984, 21, 1355
12. Bankley, C. J.; Kaltenbronn, J. S.; DeJhon, D. E.; Werner, A.; Benett, L. R.; Bobowski, G.; Krolls, U.; Johnson, D. R.; Pearlman, W. M.; Hoefle, M. L.; Essenburg, A. D.; Cohen, D. M.; Kaplan, H. R. J. Med. Chem. 1987, 30, 992
13. Beeley, L. J.; Rockell, C. J. M. Tetrahedron Lett. 1990, 31, 417
14. Gaertzen, O.; Buchwald, S. L. J. Org. Chem. 2002, 67, 465
15. Solé, D.; Serrano, O. J. Org. Chem. 2010, 75, 6267
16. Arizpe, A.; Sayago, F. J.; Jiménez, A. I.; Ordónez, M.; Cativiela, C. Eur. J. Org. Chem. 2011, 6732
17. Asymmetric Organic Synthesis with Enzymes; Gotor, V.; Alfonso, I.; García-Urdiales, E., Eds.; Wiley-VCH: Weinheim, Germany, 2008.
18. Organic Synthesis with Enzymes in Non-Aqueous Medium; Carrea, G.; Riva, S., Eds.; Wiley-VCH: Weinheim, Germany, 2008.
19. Modern Biocatalysis. Stereoselective and Environmentally Friendly Reactions; Fessner, W.-D.; Anthonsen, T., Eds.; Wiley-VCH: Weinheim, Germany, 2009.
20. Hudlicky, T.; Reed, J. W. Chem. Soc. Rev. 2009, 38, 3117
21. Liljeblad, A.; Kanerva, L. T. Tetrahedron 2006, 62, 5831-5854
22. Gotor-Fernández, V.; Gotor, V. Curr. Opin. Drug Discov. Dev. 2009, 12, 784
23. Hydrolases in Organic Synthesis: Regio-and Stereoselective Transformations, 2 nd ed.; Bornscheuer, U. T.; Kazlauskas, R. J., Eds.; Wiley-VCH: Weinheim, Germany, 2006.
24. Busto, E.; Gotor-Fernández, V.; Gotor, V. Chem. Rev. 2011, 111, 3998
25. Pietruszka, J.; Simon, R. C.; Kruska, F.; Braun, M. Eur. J. Org. Chem. 2009, 6217
26. Gotor-Fernández, V.; Fernández-Torres, P.; Gotor, V. Tetrahedron: Asymmetry 2006, 17, 2558
27. Breen, G. F. Tetrahedron: Asymmetry 2004, 15, 1427-1430
28. Pámies, O.; Bäckvall, J.-E. Chem. Rev. 2003, 103, 3247
29. Martín-Matute, B.; Bäckvall, J.-E. Curr. Opin. Chem. Biol. 2007, 11, 226
30. Ahn, Y.; Ko, S.-B.; Kim, M.-J.; Park, J. Coord. Chem. Rev. 2008, 252, 647
31. Lee, J. H.; Han, K.; Kim, M.-J.; Park, J. Eur. J. Org. Chem. 2010, 999
32. Pellisier, H. Tetrahedron 2011, 67, 3769
33. Takayama, S.; Lee, S. T.; Hung, S.-C.; Wong, C.-H. Chem. Commun. 1999, 127