Samarium dienolate mediated stereoselective synthesis of anti-1,3-diol monoesters via aldol-Tishchenko reaction

Tetrahedron Letters

Volumn 47, Issue 27, 2006, Pages 4753-4757

  Reutrakul, Vichai ^a   Jaratjaroonphong, Jaray ^a   Tuchinda, Patoomratana ^a   Kuhakarn, Chutima ^a   Kongsaeree, Palangpon ^a   Prabpai, Samran ^a   Pohmakotr, Manat ^a  

^a MAHIDOL UNIVERSITY   (Thailand)

Author keywords

Aldol Tishchenko reaction; Samarium dienolate

Indexed keywords

GLYCEROL DIOLEATE; POLYOL; SAMARIUM;

ALDOL REACTION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; REDUCTION KINETICS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION;

EID: 33744532073     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.04.091     Document Type: Article

References (44)

1. Examples of the Tishchenko reactions in natural product synthesis, see:. Romo D., Meyer S.D., Johnson D.D., and Schreiber S.L. J. Am. Chem. Soc. 115 (1993) 7906-7907
2. Wild R., and Schmidt R.R. Tetrahedron: Asymmetry 5 (1994) 2195-2208
3. Schöning K.-U., Hayashi R.K., Powell D.R., and Kirschning A. Tetrahedron: Asymmetry 10 (1999) 817-820
4. Paterson I., Davies R.D.M., and Marquez R. Angew. Chem., Int. Ed. 40 (2001) 603-607
5. Shotwell J.B., Krygowski E.S., Hines J., Koh B., Huntsman E.W.D., Choi H.W., Schneekloth Jr. J.S., Wood J.L., and Crews C.M. Org. Lett. 4 (2002) 3087-3089
6. Smith III A.B., Adams C.M., Barbosa S.A.L., and Degnan A.P. J. Am. Chem. Soc. 125 (2003) 350-351
7. Jiang Y., Hong J., and Burke S.D. Org. Lett. 6 (2004) 1445-1448
8. Törmäkangas O.P., and Koskinen A.M.P. Org. Process Res. Dev. 5 (2001) 421-425
9. Examples of tandem aldol-Tishchenko reactions, see:. Burkhardt E.R., Bergman R.G., and Heathcock C.H. Organometallics 9 (1990) 30-44
10. Curran D.P., and Wolin R.L. Synlett (1991) 317-318
11. Baramee A., Chaichit N., Intawee P., Thebtaranonth C., and Thebtaranonth Y. J. Chem. Soc., Chem. Commun. (1991) 1016-1017
12. Horiuchi Y., Taniguchi M., Oshima K., and Utimoto K. Tetrahedron Lett. 36 (1995) 5353-5356
13. Mahrwald R., and Costisella G. Synthesis (1996) 1087-1089
14. Bodnar P.M., Shaw J.T., and Woerpel K.A. J. Org. Chem. 62 (1997) 5674-5675
15. Abu-Hasanayn F., and Streitwieser A. J. Org. Chem. 63 (1998) 2954-2960
16. Lu L., Chang H.-Y., and Fang J.-M. J. Org. Chem. 64 (1999) 843-853
17. Delas C., Blacque O., and Moïse C. J. Chem. Soc., Perkin Trans. 1 (2000) 2265-2270
18. Schneider C., and Hansch M. Chem. Commun. (2001) 1218-1219
19. Simpura I., and Nevalainen V. Tetrahedron Lett. 42 (2001) 3905-3907
20. Simpura I., and Nevalainen V. Tetrahedron 59 (2003) 7535-7546
21. Schneider C., Klapa K., and Hansch M. Synlett (2005) 91-94
22. Hon Y.-S., and Chang C.-P. Tetrahedron 61 (2005) 5267-5275
23. Examples of catalytic asymmetric aldol-Tishchenko reactions, see:. Mascarenhas C.M., Miller S.P., White P.S., and Morken J.P. Angew. Chem., Int. Ed. 40 (2001) 601-603
24. Mlynarski J., and Mitura M. Tetrahedron Lett. 45 (2004) 7549-7552
25. Gnanadesikan V., Horiuchi Y., Ohshima T., and Shibasaki M. J. Am. Chem. Soc. 126 (2004) 7782-7783
26. Mlynarski J., Jankowska J., and Rakiel B. Chem. Commun. (2005) 4854-4856
27. Rohr K., Herre R., and Mahrwald R. Org. Lett. 7 (2005) 4499-4501
28. 2, see:. Evans D.A., and Hoveyda A.H. J. Am. Chem. Soc. 112 (1990) 6447-6449
29. Uenishi J., Masuda S., and Wakabayashi S. Tetrahedron Lett. 38 (1991) 5097-5100
30. Molander G.A., and McKie J.A. J. Am. Chem. Soc. 115 (1993) 5821-5822
31. Hsu J.-L., and Fang J.-M. J. Org. Chem. 66 (2001) 8573-8584
32. Fan C.-A., Wang B.-M., Tu Y.-Q., and Song Z.-L. Angew. Chem., Int. Ed. 40 (2001) 3877-3880
33. Miyano A., Tashiro D., Kawasaki Y., Sakaguchi S., and Ishii Y. Tetrahedron Lett. 39 (1998) 6901-6902
34. Reutrakul V., Saeeng R., Pohmakotr M., and Kongsaeree P. Tetrahedron Lett. 40 (1999) 1019-1020
35. 2 in organic synthesis, see:. Kagan H.B. Tetrahedron 59 (2003) 10351-10372
36. For examples of enolate formation from cyclopropyl ketones, see:. Enholm E.J., and Jia Z.J. J. Org. Chem. 62 (1997) 9159-9164
37. Molander G.A., and Harris C.R. Tetrahedron 54 (1998) 3321-3354
38. Avilov D.V., Malusare M.G., Arslancan E., and Dittmer D.C. Org. Lett. 6 (2004) 2225-2228
39. For examples of the generation and reaction of samarium dienolates, see:. Yang S.-M., and Fang J.-M. Tetrahedron Lett. 38 (1997) 1589-1592
40. Otaka A., Yukimasa A., Watanabe J., Sasaki Y., Oishi S., Tamamura H., and Fujii N. Chem. Commun. (2003) 1834-1835
41. 4, and evaporated to give an oil or a solid as a crude product.
42. Loog O., and Mäeorg U. Tetrahedron: Asymmetry 10 (1999) 2411-2415
43. Umekawa Y., Sakaguchi S., Nishiyama Y., and Ishii Y. J. Org. Chem. 62 (1997) 3409-3412
44. Jurczak J., Pikul S., and Bauer T. Tetrahedron 42 (1986) 447-488