Stereoselective synthesis of highly enantioenriched 3-methyl-2-cyclohexen-1-ones possessing an asymmetric quaternary carbon as C-4 or C-6: a sugar template approach

Tetrahedron Letters

Volumn 49, Issue 7, 2008, Pages 1203-1207

  Kubo, Hiroto ^a   Kozawa, Ikuko ^a   Takao, Ken ichi ^a   Tadano, Kin ichi ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

1,4 Addition; Aldol condensation; Intramolecular cyclization; Sugar template

Indexed keywords

3 METHYL 2 CYCLOHEXEN 1 ONE; CARBON; METHYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; ENANTIOMER; METHYLATION; POLYMERIZATION; STEREOCHEMISTRY;

EID: 38349073962     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.12.031     Document Type: Article

References (31)

1. Totani K., Takao K., and Tadano K. Synlett (2004) 2066-2680
2. Munakata R., Totani K., Takao K., and Tadano K. Synlett (2000) 979-982
3. Totani K., Asano S., Takao K., and Tadano K. Synlett (2001) 1772-1776
4. Asano S., Tamai T., Totani K., Takao K., and Tadano K. Synlett (2003) 2252-2254
5. Sasaki D., Sawamoto D., Takao K., Tadano K., Okue M., and Ajito K. Heterocycles 72 (2007) 103-110
6. Nagatsuka T., Yamaguchi S., Totani K., Takao K., and Tadano K. Synlett (2001) 481-484
7. Nagatsuka T., Yamaguchi S., Totani K., Takao K., and Tadano K. J. Carbohydr. Chem. 20 (2001) 519-535
8. Tamai T., Asano S., Totani K., Takao K., and Tadano K. Synlett (2003) 1865-1867
9. Some recent prominent papers on this subject:. Trost B.M., Pissot-Soldermann C., Chen I., and Schroeder G.M. J. Am. Chem. Soc. 126 (2004) 4480-4481
10. Trost B.M., and Xu J. J. Am. Chem. Soc. 127 (2005) 2846-2847
11. Mohr J.T., Behenna D.C., Harned A.M., and Stoltz B.M. Angew. Chem., Int. Ed. 44 (2005) 6924-6927
12. Some recent prominent papers on this subject:. Bella M., and Jørgensen K.A. J. Am. Chem. Soc. 126 (2004) 5672-5673
13. Wilson R.M., Jen W.S., and MacMillan D.W.C. J. Am. Chem. Soc. 127 (2005) 11616-11617
14. A recent review on this subject. Arya P., and Qin H. Tetrahedron 56 (2000) 917-947
15. Kozawa I., Akashi Y., Takiguchi K., Sasaki D., Sawamoto D., Takao K., and Tadano K. Synlett (2007) 399-402
16. 3) m/z 525.3068, found 525.3070.
17. 3) m/z 525.3068, found 525.3069.
18. Terashima S., Sato S., and Koga K. Tetrahedron Lett. 20 (1979) 3469-3472
19. Kreiser W., and Balow P. Tetrahedron Lett. 22 (1981) 429-432
20. Fráter G., Müller U., and Günther W. Tetrahedron 40 (1984) 1269-1277
21. 8 [the hydrazine adduct = a pyrazoline derivative (19%), 1 (77%), C-3 to C-4 silyl migrated sugar (17%)].
22. +) m/z 328.1522, found 328.1527.
23. +-H) m/z 177.0763, found 177.0764.
24. Yamazaki O., Togo H., Matsubayashi S., and Yokoyama M. Tetrahedron 55 (1999) 3735-3747
25. +) m/z 196.1099, found 196.1100.
26. R (min) = 38.1 for 16, 34.2 for (S)-16. A racemic mixture of 16 was prepared from commercial ethyl 2-methylacetoacetate y treatment with methyl vinyl ketone in MeOH in the presence of MeONa, followed by ester exchange with EtONa in EtOH.
27. R (min) = 24.2 for 19, 21.5 for (S)-19. A racemic mixture of 19 was prepared from ethyl 2-methylacetoacetate by treatment with methyl vinyl ketone in the presence of pyrrolidine/AcOH.
28. 3) m/z 525.3068, found 525.3073.
29. +) m/z 328.1522, found 328.1525.
30. 3).
31. 8 In the case of allylation and successive methylation, the diastereoselectivity was remarkably reduced to ca. 1:1.