Synthesis of enantiomerically enriched (R)- and (S)-benzofuranyl- and benzo[b]thiophenyl-1,2-ethanediols via enantiopure cyanohydrins as intermediates

Tetrahedron Asymmetry

Volumn 21, Issue 4, 2010, Pages 443-450

  Bencze, László Csaba ^a   Paizs, Csaba ^a   Toşa, Monica Ioana ^a   Vass, Elemér ^b   Irimie, Florin Dan ^a  

^a BABE BOLYAI UNIVERSITY   (Romania)

^b EÖTVÖS LORÁND UNIVERSITY   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

BENZO[B]THIOPHENYL 1,2 ETHANEDIOL; BENZOFURANYL 1,2 ETHANEDIOL; CYANOHYDRIN; ETHYLENE GLYCOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL STRUCTURE; ENANTIOMER; ENZYME KINETICS; PRIORITY JOURNAL; SYNTHESIS;

EID: 77951023384     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2010.01.018     Document Type: Article

References (48)

1. Knoll J. CNS Drug Rev. 7 (2001) 317-345
2. Krajewski K., Zhang Y., Parrish D., Deschamps J., Roller P.P., and Pathak V.K. Bioorg. Med. Chem. Lett. 16 (2006) 3034-3038
3. Queiroz M.J., Calhetha R.C., Vale-Silva L.A., Pinto E., and Nascimento M.S.-J. Eur. J. Med. Chem. 44 (2009) 1893-1899
4. Bhowmick K.C., and Joshi N.N. Tetrahedron: Asymmetry 17 (2006) 1901-1929
5. Bianchi D., Bosetti A., Cesti P., and Golini P. Tetrahedron Lett. 33 (1992) 3231-3234
6. Pye P.J., Rossen K., Weissman S.A., Maliakal A., Reamer R.A., Ball R., Tsou N.N., Volante R.P., and Reider P.J. Chem. Eur. J. 8 (2002) 1372-1376
7. Kolb H.C., Van Nieuwenhze M.S., and Sharpless K.B. Chem. Rev. 94 (1994) 2483-2547
8. Sharpless K.B., Amberg W., Bennani Y.L., Crispino G.A., Hartung J., Jeong K.-S., Kwong H.-L., Morikawa K., Wang Z.-M., Xu D., and Zhang X.-L. J. Org. Chem. 57 (1992) 2768-2771
9. Becker H., and Sharpless K.B. Angew. Chem., Int. Ed. 35 (1996) 448-451
10. Vachon J., Lauper C., Ditrichb K., and Lacour J. Tetrahedron: Asymmetry 17 (2006) 2334-2338
11. Soriente A., De Rosa M., Lamberti M., Tedesco C., Scettri A., and Pellecchia C. J. Mol. Catal. A: Chem. 235 (2005) 253-259
12. Mirkhani V., Tangestaninejad S., Yadollahi B., and Alipanah L. Tetrahedron 59 (2003) 8213-8218
13. Jacobsen E.N., Kakiuchi F., Konsler R.G., Larrow J.F., and Tokunaga M. Tetrahedron Lett. 38 (1997) 773
14. Ohkuma T., Utsumi N., Watanabe M., Tsutsumi K., Arai N., and Murata K. Org. Lett. 9 (2007) 2565-2567
15. Cross D.J., Kenny J.A., Houson I., Campbell L., Walsgrove T., and Wills M. Tetrahedron: Asymmetry 12 (2001) 1801-1806
16. Ohkuma T., Kitamura M., and Noyori R. In: Ojima I. (Ed). Catalytic Asymmetric Synthesis. 2nd ed. (2000), Wiley-VCH, New York 1-110
17. Pinheiro L., and Marsaioli A.J. J. Mol. Catal. B: Enzym. 44 (2007) 78-86
18. Raminska J.E., Smigielski K., Lobodzinska D., and Gora J. Tetrahedron: Asymmetry 11 (2000) 1211-1215
19. Virsu P., Liljebad A., Kanerva A., and Kanerva L.T. Tetrahedron: Asymmetry 12 (2000) 2447-2455
20. Lemke K., Theil F., Kunath A., and Schich H. Tetrahedron: Asymmetry 7 (1996) 971-974
21. Kamal A., and Chouhan G. Tetrahedron Lett. 45 (2004) 8801-8805
22. Simeo Y., and Faber K. Tetrahedron: Asymmetry 17 (2006) 402-409
23. Doumèche B., Archelas A., and Furstossb R. Adv. Synth. Catal. 348 (2006) 1948-1957
24. Nakamura K., Kawai Y., Oka S., and Ohno A. Tetrahedron Lett. 30 (1989) 2245
25. Nakamura K., Kawai Y., and Ohno A. Tetrahedron Lett. 31 (1990) 3631-3632
26. Bálint J., Egri G., Kolbert A., Dianóczky Cs., Fogassy E., Novák L., and Poppe L. Tetrahedron: Asymmetry 10 (1999) 4017-4028
27. Manzocchi A., Fiecchi A., and Santaniello E. J. Org. Chem. 53 (1988) 4405
28. Ferraboschi P., Grisenti P., Manzocchi A., and Santaniello E. J. Chem. Soc., Perkin Trans. 1 (1990) 2469
29. Egri G., Kolbert A., Bálint J., Fogassy E., Novák L., and Poppe L. Tetrahedron: Asymmetry 9 (1998) 271-283
30. Paizs C., Toşa M.I., Majdik C., Moldovan P., Novak L., Kolonits P., Marcovici A., Irimie F.D., and Poppe L. Tetrahedron: Asymmetry 14 (2003) 1495-1501
31. Podea P.V., Paizs C., Toşa M.I., and Irimie F.D. Tetrahedron: Asymmetry 19 (2008) 1959-1964
32. Holt J., and Hanefeld U. Curr. Org. Synth. 6 (2009) 15-37
33. Kanerva L.T., Rahiala K., and Sundholm O. Biocatalysis 10 (1994) 169-180
34. Veum L., Kanerva L.T., Halling P.J., Maschmeyer T., and Hanefeld U. Adv. Synth. Catal. (2005)
35. Paizs C., Tähtinen P., Lundell K., Poppe L., Irimie F.D., and Kanerva L.T. Tetrahedron: Asymmetry 14 (2003) 1895-1904
36. Freedman T.B., Cao X., Dukor R.K., and Nafie L.A. Chirality 15 (2003) 734-758
37. Stephens P.J., Devlin F.J., and Pan J.J. Chirality 20 (2008) 643-663
38. North M. Tetrahedron: Asymmetry 14 (2003) 147-176
39. Tosa M.I., Pilbak S., Moldovan P., Paizs C., Szatzker G., Szakacs G., Novak L., Irimie F.D., and Poppe L. Tetrahedron: Asymmetry 19 (2008) 1844-1852
40. Dziewiszek K., and Zamojski A. Carbohydr. Res. 150 (1986) 163-171
41. Effenberger F., Horsch B., Forster S., and Ziegler T. Tetrahedron Lett. 31 (1990) 1249-1252
42. Reisinger C., Osprian I., Glieder A., Schoemaker H.E., Griengl H., and Schwab H. Biotechnol. Lett. 26 (2004) 1675-1680
43. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W. Wong, M. W.; Gonzalez, C.; and Pople, J. A., Gaussian 03, Revision D.01, Gaussian, Inc., Wallingford CT, 2004.
44. Zaidlewicz M., Chechlowska A., Prewysz-Kwinto A., and Wojtczak A. Heterocycles 55 (2001) 569-577
45. King W.J., and Nord F.F. J. Org. Chem. 13 (1948) 635-637
46. Podea P.V., Tosa M.I., Paizs C., and Irimie F.D. Tetrahedron: Asymmetry 19 (2008) 500-511
47. Gassman P.G., and Talley J.J. Tetrahedron Lett. 19 (1978) 3773-3779
48. Steinreiber A., and Faber K. Curr. Opin. Biotech. 12 (2001) 552-558