A new procedure for the enantioselective vinylogous aldol reaction of Chan's diene

Tetrahedron Asymmetry

Volumn 17, Issue 24, 2006, Pages 3332-3334

  Villano, Rosaria ^a   Acocella, Maria Rosaria ^a   Massa, Antonio ^a   Palombi, Laura ^a   Scettri, Arrigo ^a  

^a UNIVERSITY OF SALERNO   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

2 PYRONE DERIVATIVE; ACETOACETIC ACID DERIVATIVE; PHOSPHORAMIDIC ACID; PHOSPHORAMIDIC ACID DERIVATIVE; SILICON DERIVATIVE; SILICON TETRACHLORIDE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; BIOLOGICAL ACTIVITY; CATALYSIS; CHEMICAL BOND; CHEMICAL STRUCTURE; CHIRALITY; ENANTIOSELECTIVITY; PRIORITY JOURNAL;

EID: 33846572483     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2006.12.016     Document Type: Article

References (39)

1. Chan T.H., and Brownbridge P. J. Chem. Soc., Chem. Commun. (1979) 578-579
2. For recent reviews, see:. Langer P. Chem. Eur. J. 7 (2001) 3858-3866
3. Langer P. Synthesis 4 (2002) 441-459
4. Soriente A., De Rosa M., Villano R., and Scettri A. Curr. Org. Chem. 8 (2004) 993-1007
5. Hagiwara H., Kon-no M., and Uda H. J. Chem. Soc., Chem. Commun. (1992) 866-868
6. Hagiwara H., Kimura K., and Uda H. J. Chem. Soc., Perkin Trans. (1992) 693-700
7. Evans D.A., and Black W.C. J. Am. Chem. Soc. 114 (1992) 2260-2262
8. Enders D., Burkamp F., and Runsink J.J. Chem. Commun. (1996) 609-610
9. Lattman E., Coombs J., and Hoffmann H.M.R. Synthesis (1996) 171-177
10. Evans D.A., Carter P.H., Carreira E.M., Prunet J.A., Charette A.B., and Lautens M. Angew. Chem., Int. Ed. 37 (1998) 2354-2359
11. Soriente A., De Rosa M., Apicella A., Scettri A., and Sodano G. Tetrahedron: Asymmetry 10 (1999) 4481-4484
12. Soriente A., De Rosa M., Villano R., and Scettri A. Tetrahedron: Asymmetry 11 (2000) 2255-2258
13. Soriente A., De Rosa M., Stanzione M., Villano R., and Scettri A. Tetrahedron: Asymmetry 12 (2001) 959-963
14. Villano R., De Rosa M., Salerno C., Soriente A., and Scettri A. Tetrahedron: Asymmetry 13 (2002) 1949-1952
15. Villano R., Acocella M.R., De Rosa M., Soriente A., and Scettri A. Tetrahedron: Asymmetry 15 (2004) 2421-2424
16. Acocella M.R., De Rosa M., Massa A., Palombi L., Villano R., and Scettri A. Tetrahedron 61 (2005) 4091-4097
17. Denmark S.E., Winter S.B.D., Su X., and Wong K.T. J. Am. Chem. Soc. 118 (1996) 7404-7405
18. Denmark S.E., Wong K.T., and Stavenger R.A. J. Am. Chem. Soc. 119 (1997) 2333-2334
19. Denmark S.E., Stavenger R.A., and Wong K.T. J. Org. Chem. 63 (1998) 918-919
20. Denmark S.E., Stavenger R.A., Wong K.T., and Su X. J. Am. Chem. Soc. 121 (1999) 4982-4991
21. Denmark S.E., and Fujimori S. Synlett (2001) 1024-1029
22. Denmark S.E., and Fan Y. J. Am. Chem. Soc. 124 (2002) 4233-4235
23. Denmark S.E., Wynn T., and Beutner G.L. J. Am. Chem. Soc. 124 (2002) 13405-13407
24. Denmark S.E., and Fujimori S. Org. Lett. 4 (2002) 3477-3480
25. Denmark S.E., and Heemstra Jr. J.R. Org. Lett. 5 (2003) 2303-2306
26. Denmark S.E., and Beutner G.L. J. Am. Chem. Soc. 125 (2003) 7800-7801
27. Denmark S.E., and Heemstra Jr. J.R. Synlett 13 (2004) 2411-2416
28. Denmark S.E., Heemstra Jr. J.R., and Beutner G.L. Angew. Chem., Int. Ed. 44 (2005) 4682-4698
29. Denmark S.E., and Heemstra Jr. J.R. J. Am. Chem. Soc. 128 (2006) 1038-1039
30. Denmark S.E., Pham S.M., Stavenger R.A., Su X., Wong K.T., and Nishigaichi Y. J. Org. Chem. 71 (2006) 3904-3922
31. 13
32. Xu C., and Yuan C. Tetrahedron 61 (2005) 2169-2186
33. Friese J., and Gleitz J. Planta Med. 64 (1998) 458-459
34. Wang F.-D., and Yue J.-M. Synlett (2005) 2077-2079
35. For enantioselective synthesis of (+)-kavain, see:. Smith T.E., Djang M., Velander A.J., Downey C.W., Carroll K.A., and Alphen S.V. Org. Lett. 6 (2004) 2317-2323
36. Wang F.-D., and Yue J.-M. Synlett 13 (2005) 2077-2079
37. Sabitha G., Sudhakar K., and Yadav J.S. Tetrahedron Lett. 47 (2006) 8599-8602
38. 4 and concentrated. The residue was purified by non-flash chromatography (petroleum ether/AcOEt 1/1) to give product (+)-6 (whose structure was confirmed by spectroscopic data) with unchanged ee (75% ee) in 75% overall yield from (R)-2b.
39. Kruger J., and Carreira E.M. J. Am. Chem. Soc. 120 (1998) 837-838