Stereoselective vinylogous Mukaiyama aldol reaction of α-haloenals

Chemical and Pharmaceutical Bulletin

Volumn 59, Issue 4, 2011, Pages 522-524

  Iwasaki, Yoichi ^a   Matsui, Ryosuke ^a   Suzuki, Takahiro ^a   Nakazaki, Atsuo ^a   Kobayashi, Susumu ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

Author keywords

haloenal; Cross coupling; Stereoselectivity; Vinylogous Mukaiyama aldol reaction

Indexed keywords

ALDEHYDE DERIVATIVE; ALPHA BROMOENAL; ALPHA CHLOROENAL; ALPHA IODOENAL; HALOGEN; PALLADIUM; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; MUKAIYAMA REACTION; STEREOCHEMISTRY;

ALDEHYDES; CATALYSIS; PALLADIUM; STEREOISOMERISM;

EID: 79953662443     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.59.522     Document Type: Article

References (31)

1. Shirokawa S.-i., Kamiyama M., Nakamura T., Okada M., Nakazaki A., Hosokawa S., Kobayashi S., J. Am. Chem. Soc., 126, 13604-13605 (2004).
2. Shinoyama M., Shirokawa S.-i., Nakazaki A., Kobayashi S., Org. Lett., 11, 1277-1280 (2009).
3. Yamaoka M., Nakazaki A., Kobayashi S., Tetrahedron Lett., 51, 287-289 (2010).
4. Hosokawa S., Ogura T., Togashi H., Tatsuta K., Tetrahedron Lett., 46, 333-337 (2005).
5. Hosokawa S., Yokota K., Imamura K., Suzuki Y., Kawarasaki M., Tatsuta K., Tetrahedron Lett., 47, 5415-5418 (2006).
6. Hosokawa S., Kuroda S., Imamura K., Tasuta K., Tetrahedron Lett., 47, 6183-6186 (2006).
7. Jiang X., Liu B., Lebreton S., De Brabander J. K., J. Am. Chem. Soc., 129, 6386-6387 (2007).
8. Nicolaou K. C., Guduru R., Sun Y.-P., Banerji B., Chen D. Y.-K., Angew. Chem. Int. Ed., 46, 5896-5900 (2007).
9. Nicolaou K. C., Sun Y.-P., Guduru R., Banerji B., Chen D. Y.-K., J. Am. Chem. Soc., 130, 3633-3644 (2008).
10. Schmauder A., Müller S., Maier M. E., Tetrahedron, 64, 6263-6269 (2008).
11. Hosokawa S., Yokota K., Imamura K., Suzuki Y., Kawarasaki M., Tatsuta K., Asian J. Chem., 3, 1415-1421 (2008).
12. Lipshutz B. H., Amorelli B., J. Am. Chem. Soc., 131, 1396-1397 (2009).
13. Wang L., Gong J., Deng L., Xiang Z., Chen Z., Wang Y., Chen J., Yang Z., Org. Lett., 11, 1809-1812 (2009).
14. Hosokawa S., Mukaeda Y., Kawahara R., Tatsuta K., Tetrahedron Lett., 50, 6701-6704 (2009).
15. Hosokawa S., Matsushita K., Tokimatsu S., Toriumi T., Suzuki Y., Tatsuta K., Tetrahedron Lett., 51, 5532-5536 (2010).
16. Paterson I., Kan S. B. J., Gibson L. J., Org. Lett., 12, 3724-3727 (2010).
17. Wang L., Xi Y., Yang S., Zhu R., Liang Y., Chen J., Yang Z., Org. Lett., 13, 74-77 (2011).
18. Tatsuta K., Hosokawa S., Chem. Rev., 105, 4707-4729 (2005).
19. Tatsuta K., Hosokawa S., Chem. Rec., 6, 217-233 (2006).
20. Hosokawa S., Tatsuta K., Mini-Rev. Org. Chem., 5, 1-18 (2008).
21. Nakamura T., Shirokawa S.-i., Hosokawa S., Nakazaki A., Kobayashi S., Org. Lett., 8, 677-679 (2006).
22. Shirokawa S.-i., Shinoyama M., Ooi I., Hosokawa S., Nakazaki A., Kobayashi S., Org. Lett., 9, 849-852 (2007).
23. Yamaoka M., Fukatsu Y., Nakazaki A., Kobayashi S., Tetrahedron Lett., 50, 3849-3852 (2009).
24. Yamaoka M., Nakazaki A., Kobayashi S., Tetrahedron Lett., 50, 6764-6768 (2009).
25. Matsui R., Seto K., Sato Y., Suzuki T., Nakazaki A., Kobayashi S., Angew. Chem. Int. Ed., 50, 680-683 (2011).
26. Krafft M. E., Cran J. W., Synlett, 8, 1263-1266 (2005).
27. Lutjens H., Nowotny S., Knochel P., Tetrahedron Asymmetry, 6, 2675-2678 (1995).
28. Kamigata N., Satoh T., Yoshida M., Bull. Chem. Soc. Jpn., 61, 449-454 (1988).
29. Ley S. V., Whittle A. J., Tetrahedron Lett., 22, 3301-3304 (1981).
30. Especially, the electron-withdrawing ability of chloro group probably shortened the reaction time in the VMAR of α-chloroenal 3c.
31. Nicolaou K. C., Papahatjis D. P., Claremon D. A., Magolda R. L., Dolle R. E., J. Org. Chem., 50, 1440-1456 (1985).