A stereoselective approach to optically active butenolides by Horner-Wadsworth-Emmons olefination reaction of α-hydroxy ketones

Tetrahedron Asymmetry

Volumn 18, Issue 15, 2007, Pages 1780-1787

  Krawczyk, Ewa ^a   Koprowski, Marek ^a   Łuczak, Jerzy ^a  

^a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA HYDROXY KETONE DERIVATIVE; AROMATIC COMPOUND; BUTENOLIDE; KETONE DERIVATIVE; LACTONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; ENANTIOMER; ESTERIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HORNER WADSWORTH EMMONS REACTION; PHOSPHORUS NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

EID: 34548410437     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2007.07.027     Document Type: Article

References (65)

1. Lin G., Chan S.S.-K., Chung H.-S., and Li S.-L. Chemistry and Biological Action of Natural Occurring Phthalides. In: Atta-ur-Rahman (Ed). Studies in Natural Products Chemistry Vol. 32 (2005), Elsevier, Amsterdam 611
2. Rao Y.S. Chem. Rev. 76 (1976) 625-694
3. Kapferer T., Bruckner R., Herzig A., and Konig W.A. Chem. Eur. J. 11 (2005) 2154-2162 and references cited therein
4. For review see:. Zografos A.L., and Georgiadis D. Synthesis (2006) 3157-3188 and references cited therein
5. Trost B.M., and Crawley M.L. Chem. Eur. J. 10 (2004) 2237-2252
6. Nagamitsu T., Takano D., Shiomi K., Ui H., Yamaguchi Y., Masuma R., Harigaya Y., Kuwajima I., and Omura S. Tetrahedron Lett. 44 (2003) 6441-6444
7. Enders D., Dyker H., and Leusink F.R. Chem. Eur. J. 4 (1998) 311-320 and references cited therein
8. Kitajima H., Ito K., and Katsuki T. Tetrahedron 53 (1997) 17015-17028 and references cited therein
9. For reviews, see:. Rao Y.S. Chem. Rev. 64 (1964) 353 and Ref. 1b
10. Recent syntheses of butenolides include the following:. Ma S., and Shi Z. J. Org. Chem. 63 (1998) 6387-6389 and references cited therein
11. Katritzky A.R., Feng D., and Lang H.J. Org. Chem. 62 (1997) 715-720
12. Sapountzis I., Dohle W., and Knochel P. Chem. Commun. (2001) 2068-2069
13. Villemin D., Cheikh N., Mostefa-Kara B., Bar N., Choukchou-Braham N., and Didi M.A. Tetrahedron Lett. 47 (2006) 5519-5521 and references cited therein
14. Tanikaga R., Hosoya K., and Kaji A. Synthesis (1987) 389-390
15. Brandange S., Flodman L., and Norberg A. J. Org. Chem. 49 (1984) 927-928
16. Booth P.M., Fox C.M.J., and Ley S.V.J. J. Chem. Soc., Perkin Trans. 1 (1987) 121-129
17. Villemin D., and Liang L. Tetrahedron Lett. 37 (1996) 8733-8734
18. Avetisyan A.A., Mangasaryan Ts.A., Melikian G.S., Dangyan M.T., and Matsoyan S.G. Zh. Org. Khim. 7 (1971) 962-964
19. Chem. Abstr. 75 (1971) 63047 q
20. Selected references since 1989:. Kocovsky P., and Stieborova I. Tetrahedron Lett. 30 (1989) 4295-4298
21. Mikołajczyk M., and Midura W.H. Synlett (1991) 245-247
22. Nagina A., and Rao P.B. Tetrahedron Lett. 33 (1992) 2375-2378
23. Bonadies F., Cardilli A., Lattanzi A., Pesci S., and Scettri A. Tetrahedron Lett. 36 (1995) 2839-2840
24. Kumar P., and Saravanan K. Tetrahedron 54 (1998) 2161-2168
25. Demir A.S., Camkerten N., Gercek Z., Duygu N., Reis O., and Arikan E. Tetrahedron 55 (1999) 2441-2448
26. Suzuki Y., Ohara A., Sugaya K., Takao K.-i., and Tadano K.-i. Tetrahedron 57 (2001) 7291-7301
27. Beck B., Magnin-Lachaux M., Herdtweck E., and Domling A. Org. Lett. 3 (2001) 2875-2878
28. Clive D.L.J., and Huang X. Tetrahedron 58 (2002) 10243-10250
29. Selected references since 1998:. Nishikori H., Ito K., and Katsuki T. Tetrahedron: Asymmetry 9 (1998) 1165-1170
30. Tan L., Chen Ch.-y., Larsen R.D., Verhoeven T.R., and Reider P.J. Tetrahedron Lett. 39 (1998) 3961-3964
31. Kiegiel J., Nowacki J., Tarnowska A., Stachurska M., and Jurczak J. Tetrahedron Lett. 41 (2000) 4003-4006
32. Ma S., and Wu S. Chem. Commun. (2001) 441-442 and references cited therein
33. Ma S., and Shi Z. Chem. Commun. (2002) 540-541 and references cited therein
34. Tan L., Chen Ch.-y., Chen W., Frey L., King A.O., Tillyer R.D., Xu F., Zhao D., Grabowski E.J.J., Reider P.J., O'Shea P., Dagneau P., and Wang X. Tetrahedron 58 (2002) 7403-7410
35. Movassaghi M., and Jacobsen E.N. J. Am. Chem. Soc. 124 (2002) 2456-2457
36. Brown S.P., Goodwin N.C., and MacMillan D.W.C. J. Am. Chem. Soc. 125 (2003) 1192-1194 and references cited therein
37. Montana A.M., Garcia F., and Batalla C. Tetrahedron Lett. 45 (2004) 8549-8552
38. Ma S., and Gu Z. J. Am. Chem. Soc. 127 (2005) 6182-6813
39. Bassora B.K., Da Costa C., Ganiani R.A., Comasseto J.V., and Dos Santos A.A. Tetrahedron Lett. 48 (2007) 1485-1487
40. Selected references:. Ireland R.E., and Varney M.D. J. Org. Chem. 51 (1986) 635-648
41. Witiak D.T., and Tehim A.K. J. Org. Chem. 55 (1990) 1112-1114 and references cited therein
42. Krawczyk E., Koprowski M., Skowrońska A., and Łuczak J. Tetrahedron: Asymmetry 15 (2004) 2599-2602
43. Koprowski M., Łuczak J., and Krawczyk E. Tetrahedron 62 (2006) 12363-12374
44. Aristoff P.A. J. Org. Chem. 46 (1981) 1954-1957
45. Blanchette M.A., Choy W., Davis J.T., Essenfeld A.P., Masamune S., Roush W.R., and Sakai T. Tetrahedron Lett. 25 (1984) 2183-2186
46. Ranade A.C., Mali R.S., and Kurnawal V.M. Indian J. Chem. Sect. B 23 (1984) 514-517
47. Zubaidha P.K., Chavan S.P., Racheria U.S., and Ayyangar N.R. Tetrahedron 47 (1991) 5759-5768
48. Chavan S.P., Zubaidha P.K., and Ayyangar N.R. Tetrahedron Lett. 33 (1992) 4605-4608
49. Chavan S.P., Zubaidha P.K., Govande Ch.A., and Subba Rao Y.T. J. Chem. Soc., Chem. Commun. (1994) 1101-1102
50. Silveira C.C., Machado A., Braga A.L., and Lenardao E.J. Tetrahedron Lett. 45 (2004) 4077-4080
51. Chavan S.P., Thakkar M., and Kalkote U.R. Tetrahedron Lett. 48 (2007) 643-646
52. Coutrot P., Snoussi M., and Savignac P. Synthesis (1978) 133-134
53. Coutrot P., and Ghribi A. Synthesis (1986) 661-664
54. Hanson R.M., and Sharpless K.B. J. Org. Chem. 51 (1986) 1922-1925
55. Kita Y., and Sekihachi J. J. Org. Chem. 55 (1990) 1108-1112
56. Metz G., and Schwenker G. Synthesis (1980) 394-397
57. Okazaki R. J. Org. Chem. 49 (1984) 3819-3824
58. Guenther H.J., Guntrum E., and Jager V. Liebigs Ann. Chem. 1 (1984) 15-30
59. Gill G.B., Sum H.J., and Idris M. Tetrahedron Lett. 26 (1985) 4811-4814
60. Bestman H.J., Schmid G.S., Guenter S., Sandmeier D., Schade G., and Oechsner H. Chem. Ber. 118 (1985) 1709-1719
61. Duerr S., Hoehlein U., and Schober R. J. Organomet. Chem. 458 (1993) 89-96
62. Tankard M.H., and Whitehurst J.S. Tetrahedron 30 (1974) 451-454
63. Delaunay J., Orliac-Le Moing A., and Simonet J. Tetrahedron 44 (1988) 7089-7094
64. Feit B.A., Melamed V., Schmidt R., and Speer H. J. Chem. Soc., Perkin Trans. 1 (1981) 1329-1338
65. Mueller P., and Graenicher Ch. Helv. Chim. Acta (1993) 521-534