Enantioselective synthesis of 2-alkylidenetetrahydrofurans based on a 'cyclization/enzymatic resolution' strategy

Tetrahedron Asymmetry

Volumn 17, Issue 6, 2006, Pages 892-899

  Bellur, Esen ^a,b   Böttcher, Dominique ^a   Bornscheuer, Uwe ^a   Langer, Peter ^b,c  

^a UNIVERSITY OF GREIFSWALD   (Germany)

^b UNIVERSITY OF ROSTOCK   (Germany)

^c LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; ENANTIOMER; ENZYME CHEMISTRY; ENZYME KINETICS; PRIORITY JOURNAL;

EID: 33646107857     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.03.006     Document Type: Article

References (55)

1. For cycloadditions, see:. Weichert A., and Hoffmann H.M.R. J. Org. Chem. 56 (1991) 4098
2. Tchelitcheff P. Bull. Soc. Chim. Fr. (1954) 672
3. Ireland R.E., and Haebich D. Chem. Ber. 114 (1981) 1418
4. Audrain H., Thorhauge J., Hazell R.G., and Joergensen K.A. J. Org. Chem. 65 (2000) 4487
5. For cycloadditions, see:. Detty M.R. J. Org. Chem. 44 (1979) 2073
6. Batra S., Srivastava S., Singh K., Chander R., Khanna A.K., and Bhaduri A.P. Bioorg. Med. Chem. 8 (2000) 2195
7. for cyclopropanations:. Kirmse W., and Rode K. Chem. Ber. 120 (1987) 847
8. for oxidative carbonylations:. Strauch H.C., Erker G., and Fröhlich R. J. Organomet. Chem. 593-594 (2000) 388
9. Kato K., Nishimura A., Yamamoto Y., and Akita H. Tetrahedron Lett. 42 (2001) 4203
10. Kato K., Tanaka M., Yamamoto Y., and Akita H. Tetrahedron Lett. 43 (2002) 1511
11. for hydrogenations. Ohta T., Miyake T., Seido N., Kumobayashi H., and Takaya H. J. Org. Chem. 60 (1995) 357 see also Ref. 2
12. Reviews:. Oivin T.L.B. Tetrahedron 43 (1987) 3309
13. Barrett A.G.M., and Sheth H.G. J. Org. Chem. 48 (1983) 5017
14. Rao Y.S. Chem. Rev. 76 (1976) 625
15. Pattenden G. Prog. Chem. Nat. Prod. 35 (1978) 133
16. Knight D.W. Contemp. Org. Synth. 1 (1994) 287
17. Gerlach H., and Wetter H. Helv. Chim. Acta 57 (1974) 2306
18. Schmidt U., Gombos J., Haslinger E., and Zak H. Chem. Ber. 109 (1976) 2628
19. Bartlett P.A., Meadows J.D., and Ottow E. J. Am. Chem. Soc. 106 (1984) 5304
20. Lygo B. Tetrahedron 44 (1988) 6889
21. Methyl nonactate:. Ahmar M., Duyck C., and Fleming I. Pure Appl. Chem. 66 (1994) 2049
22. also see for (-)-nonactic acid:. Fraser B., and Perlmutter P. J. Chem. Soc., Perkin Trans. 1 (2002) 2896
23. Spiroketal chalcogran:. Ley S.V., Lygo B., Organ H.M., and Wonnacott A. Tetrahedron 41 (1985) 3825
24. Booth P.M., Fox C.M.J., and Ley S.V. J. Chem. Soc., Perkin Trans. 1 (1987) 121
25. Mori K., Sasaki M., Tamada S., Suguro T., and Masuda S. Tetrahedron 35 (1979) 1601
26. For reviews of cyclization reactions of free and masked dianions, see:. Langer P. Chem. Eur. J. 7 (2001) 3858
27. Langer P. Synthesis (2002) 441
28. Langer P., and Freiberg W. Chem. Rev. 104 (2004) 4125
29. Langer P., Holtz E., Karimé I., and Saleh N.N.R. J. Org. Chem. 66 (2001) 6057
30. Langer P., and Bellur E. J. Org. Chem. 68 (2003) 9742
31. see also:. Edwards G.L., and Sinclair D.J. Tetrahedron Lett 40 (1999) 3933
32. Krueger S.A., and Bryson T.A. J. Org. Chem. 39 (1974) 3167
33. Gabriele B., Salerno G., De Pascali F., Costa M., and Chiusoli G.P. J. Organomet. Chem. 593-594 (2000) 409
34. Pflieger D., and Muckensturn B. Tetrahedron 45 (1989) 2031
35. Tsujita H., Ura Y., Wada K., Kondo T., and Mitsudo T.-A. Chem. Commun. (2005) 5100
36. Sharma G.V.M., Punna S., Hymavathi L., Reddy N.Y., Krishna P.R., Chorghadeb M.S., and Ley S.V. Tetrahedron: Asymmetry 16 (2005) 1135
37. Bellur E., and Langer P. Synlett (2004) 2169
38. Bellur E., and Langer P. Eur. J. Org. Chem. (2005) 4815
39. Bellur E., and Langer P. Synthesis 3 (2006) 480
40. Bellur E., and Langer P. Synlett (2004) 2172
41. Bellur E., and Langer P. J. Org. Chem. 70 (2005) 3819
42. Bellur E., and Langer P. J. Org. Chem. 70 (2005) 7686
43. Bellur E., Freifeld I., and Langer P. Tetrahedron Lett. 46 (2005) 2185
44. Bellur E., and Langer P. J. Org. Chem. 70 (2005) 10013
45. Bellur E., Görls H., and Langer P. Eur. J. Org. Chem. (2005) 2074
46. see also:. Langer P., and Krummel T. Chem. Eur. J. 7 (2001) 1720
47. Langer P., Armbrust H., Eckardt T., and Magull J. Chem. Eur. J. 8 (2002) 1443
48. Review for Candida antarctica lipase B (CAL-B):. Anderson E.M., Larsson K.M., and Kirk O. Biocatal. Biotrans. 16 (1998) 181
49. Reviews/books about enzymes in organic synthesis:. Bornscheuer U.T., and Kazlauskas R.J. Hydrolases in Organic Synthesis-Regio- and Stereoselective Biotransformations (2005), Wiley-VCH, Weinheim
50. Davis B.G., and Boyer V. Nat. Prod. Rep. 18 (2001) 618
51. Faber K. Pure Appl. Chem. 69 (1997) 1613
52. Reactions of diazomethane with the vinyl group:. Firestone R.A. J. Org. Chem. 41 (1976) 2212
53. Rastelli A., Gandolfi R., and Amadè M.S. J. Org. Chem. 63 (1998) 7425
54. Stevens C., Gallant M., and De Kimpe N. Tetrahedron Lett. 40 (1999) 3457
55. Kozyrev A.N., Alderfer J.L., and Robinson B.C. Tetrahedron 59 (2003) 499