The first synthesis of both enantiomers of 2-hydroxycyclobutanone acetals by enzymatic transesterification: Preparation of (R)-(+)-2- benzyloxycyclobutanone and its antipode

Tetrahedron Asymmetry

Volumn 15, Issue 11, 2004, Pages 1711-1718

  Hazelard, Damien ^a   Fadel, Antoine ^a   Morgant, Georges ^b  

^a UNIVERSITÉ PARIS SUD   (France)

^b UNIVERSITÉ PARIS SACLAY   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 BENZYLOXYCYCLOBUTANONE; CYCLOBUTANONE DERIVATIVE; ENZYME; HYDROXYL GROUP; NAPROXEN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; ENANTIOMER; PRIORITY JOURNAL; PROTECTION; REACTION ANALYSIS; SYNTHESIS; TRANSESTERIFICATION; X RAY ANALYSIS;

EID: 2942598065     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetasy.2004.04.016     Document Type: Article

References (53)

1. Conia J.-M., Sandre J.-P. Bull. Soc. Chim. Fr. 1963;744
2. Vidal J., Huet F. J. Org. Chem. 53:1988;611
3. Cohen T., Ouellette D., Senaratne K.P.A., Yu L.-C. Tetrahedron Lett. 22:1981;3377
4. Shevchuk T.A., Kulinkovich O.G. Russ. J. Org. Chem. 36:2000;491
5. Wassermann H.H., Hearn M.J., Cochoy R.E. J. Org. Chem. 45:1980;2874
6. For optically active cyclobutanones, see: Fitjer L. Cyclobutanes. de Meijere A. Synthesis: by Ring Enlargement. Houben-Weyl (Methods of Organic Chemistry). Vol. E 17e:1997;251 Thieme, Stuttgart
7. Cho S.Y., Cha J.K. Org. Lett. 2:2000;1337
8. Yoshida M., Ismail M.A.H., Nemoto H., Ihara M. J. Chem. Soc., Perkin Trans. 1. 2000;2629
9. Nemoto H., Miyata J., Hakamata H., Fukumoto K. Tetrahedron Lett. 36:1995;1055
10. Nemoto H., Miyata J., Hakamata H., Nagamochi M., Fukumoto K. Tetrahedron. 51:1995;5511
11. Krief A., Ronvaux A., Arounarith T. Tetrahedron. 54:1998;6903
12. Rouge P.D., Moglioni A.G., Moltrasio G.Y., Ortuño R.M. Tetrahedron: Asymmetry. 14:2003;193
13. Ollivier J., Legros J.-Y., Fiaud J.-C., de Meijere A., Salaün J. Tetrahedron Lett. 31:1990;4135
14. Fadel A., Khesrani A. Tetrahedron: Asymmetry. 9:1998;305
15. Fadel A., Tesson N. Eur. J. Org. Chem. 2000;2153
16. Tesson N., Dorigneux B., Fadel A. Tetrahedron: Asymmetry. 13:2002;2267
17. Truong M., Lecornué F., Fadel A. Tetrahedron: Asymmetry. 14:2003;1063. and references cited therein
18. Salaün J., Fadel A., Conia J.M. Tetrahedron Lett. 1979;1429
19. For specialized books see: Poppe L., Novàk L. Selective Biocatalysis: a Synthetic approach. 1992;VCH, Weinheim
20. For reviews see: Boland W., Forössl C., Lorenz M. Synthesis. 1991;1049
21. Banfi L., Guanti G. Synthesis. 1993;1029
22. Azerad R. Bull. Soc. Chim. Fr. 132:1995;17
23. Schoffers E., Golebiowski A., Johnson C.R. Tetrahedron. 52:1996;3769. and references cited therein
24. Therisod M., Klibanov A.M. J. Am. Chem. Soc. 108:1986;5638. and references cited therein
25. Rühlmann K. Synthesis. 1971;236. and references cited therein
26. Bloomfield J.J., Nelke J.M. Org. Synth. 57:1977;1
27. Conia J.M., Barnier J.P. Terahedron Lett. 1971;4981
28. Barnier J.P., Denis J.M., Salaün J., Conia J.M. Tetrahedron. 30:1974;1405
29. Fadel A., Yefsah R., Salaün J. Synthesis. 1987;37
30. Easwar S., Desai S.B., Argade N.P., Ganesh K.N. Tetrahedron: Asymmetry. 13:2002;1367
31. Bovara R., Carrera G., Ferrara L., Riva S. Tetrahedron: Asymmetry. 2:1991;931
32. p)
33. Huet F., Lechevallier A., Pellet M., Conia J.M. Synthesis. 1978;63
34. For racemic compound, see: Bisel Ph., Breiting E., Frahm A.W. Eur. J. Org. Chem. 1998;729
35. Green, F. R. III; Olyslager, R. J. E. Eur. Patent Appl. EP 280.232, 1988; Chem. Abstr. 1989, 110, 37813h
36. Fadel A., Arzel Ph. Tetrahedron: Asymmetry. 8:1997;283
37. Mitsunobu O. Synthesis. 1981;1
38. Vänttinen E., Kanerva L.T. Tetrahedron: Asymmetry. 6:1995;1779
39. Virsu P., Liljeblad A., Kanerva A., Kanerva L.T. Tetrahedron: Asymmetry. 12:2001;2447
40. 23 in good yield
41. Piccolo, O.; Valoti, E.; Visentin, G. (Zambon group) EP 0163338 A1 19851204, CAN 105: 60435, AN 1986: 460435
42. Piccolo O., Spreafico F., Visentin G. J. Org. Chem. 52:1987;10
43. Yu G., Mason H.J., Galdi K., Wu X., Cornelius L., Zhao N., Witkus M., Ewing W.R., Macor J.E. Synthesis. 2003;403
44. Watson W.D. J. Org. Chem. 50:1985;2145
45. Crystallographic data for compound ( + )-10 has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 232786. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK. Fax: +44-1233-336033, e-mail: deposit@ccdc.cam.ac.uk.
46. For recent reports of the enantioselectivity of Candida antarctica lipase for the (R)-isomer: see Forro' E., Kanerva L.T., Fülöp F. Tetrahedron: Asymmetry. 9:1998;513
47. Conti P., Dallanoce C., De Amici M., De Micheli C., Carrea G., Zambianci F. Tetrahedron: Asymmetry. 9:1998;657
48. Ziegler T., Bien F., Jurisch C. Tetrahedron: Asymmetry. 9:1998;765
49. Conde S., Fierros M., Rodriguez-Franco M.I., Puig C. Tetrahedron: Asymmetry. 9:1998;2229
50. Bit C., Mitrochkine A.A., Gil G., Pierrot M., Réglier M. Tetrahedron: Asymmetry. 9:1998;3263
51. For crystallographic data of lipase B from Candida antarctica, which reveal a stereoscopic pocket for secondary alcohols: see Uppenberg J., Öhrner N., Norin M., Hult K., Kleywegt G.J., Patkar S., Waagen V., Anthonsen T., Jones T.A. Biochemistry. 35:1995;16838
52. SIR92, A program for crystal structure solution: Altamore A., Cascarano G., Giacovazzo C., Guagliardi A. J. Appl. Crystallogr. 26:1993;343
53. CRYSTALS (2001): Watkin, D. J.; Prout, C. K.; Carruthers, J. R.; Betteridge, P. W.; Cooper, R. I. Issue 11, Chemical Crystallography Laboratory, Oxford, UK