Asymmetric Rh-catalyzed intermolecular hydroacylation of 1,5-hexadiene with salicylaldehyde

Chemical and Pharmaceutical Bulletin

Volumn 57, Issue 10, 2009, Pages 1158-1160

  Inui, Yasuhiro ^a   Tanaka, Masakazu ^a,b   Imai, Masanori ^c   Tanaka, Keitaro ^a   Suemune, Hiroshi ^a  

^a KYUSHU UNIVERSITY   (Japan)

^b NAGASAKI UNIVERSITY   (Japan)

^c HOKKAIDO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

Chelation; Enantioselective reaction; Intermolecular hydroacylation; Rhodium

Indexed keywords

1,5 HEXADIENE; ALKADIENE; PHOSPHINE DERIVATIVE; RHODIUM; SALICYLALDEHYDE; UNCLASSIFIED DRUG; ZINC BROMIDE;

ACYLATION; ARTICLE; ASYMMETRIC CATALYSIS; CATALYST; CHEMICAL REACTION; CHIRALITY; CYCLIZATION; ENANTIOMER; ISOMER;

ALDEHYDES; ALKADIENES; BROMIDES; CATALYSIS; NAPHTHALENES; ORGANOMETALLIC COMPOUNDS; RHODIUM; STEREOISOMERISM; ZINC COMPOUNDS;

EID: 70349675591     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.57.1158     Document Type: Article

References (39)

1. Sakai K., Ide J., Oda O., Nakamura N., Tetrahedron Lett., 13, 1287-1290 (1972).
2. Fairlie D. P., Bosnich B., Organometallics, 7, 936-945 (1988).
3. Aloise A. D., Layton M. E., Shair M. D., J. Am. Chem. Soc., 122, 12610-12611 (2000).
4. Bendorf H. D., Colella C. M., Dixon E. C., Marchetti M., Matukonis A. N., Musselman J. D., Tiley T. A., Tetrahedron Lett., 43, 7031-7034 (2002).
5. Sato Y., Oonishi Y., Mori M., Angew. Chem., Int. Ed., 41, 1218-1221 (2002).
6. Takeishi K., Sugishima K., Sasaki K., Tanaka K., Chem. Eur. J., 10, 5681-5688 (2004).
7. Hyatt I. F. D., Anderson H. K., Morehead A. T. Jr., Sargent A. L., Organometallics, 27, 135-147 (2008).
8. Kokubo K., Matsumasa K., Nishinaka Y., Miura M., Nomura M., Bull. Chem. Soc. Jpn., 72, 303-311 (1999).
9. Miura M., Nomura M., J. Synth. Org. Chem. Jpn., 58, 578-586 (2000).
10. Jun C.-H., Hong J.-B., Lee D.-Y., Synlett, 1999, 1-12 (1999).
11. Jun C.-H., Lee D.-Y., Lee H., Hong J.-B., Angew. Chem. Int. Ed., 39, 3070-3072 (2000).
12. Jun C.-H., Moon C. W., Lee D.-Y., Chem. Eur. J., 8, 2422-2428 (2002).
13. Jun C.-H., Moon C. W., Lee H., Lee D.-Y., J. Mol. Cat. A: Chem., 189, 145-156 (2002).
14. Willis M. C., McNally S. J., Beswick P. J., Angew. Chem. Int. Ed., 43, 340-343 (2004).
15. Willis M. C., Randell-Sly H. E., Woodward R. L., McNally S. J., Currie G. S., J. Org. Chem., 71, 5291-5297 (2006).
16. Hong Y.-T., Barchuk A., Krische M. J., Angew. Chem. Int. Ed., 45, 6885-6888 (2006).
17. Jun C.-H., Jo E.-A., Park J.-W., Eur. J. Org. Chem., 2007, 1869-1881 (2007).
18. Tanaka K., Shibata Y., Suda T., Hagiwara Y., Hirano M., Org. Lett., 9, 1215-1218 (2007).
19. Shimizu M., Tsurugi H., Satoh T., Miura M., Chem. Asian J., 3, 881-886 (2008).
20. Our asymmetric Rh-catalyzed intramolecular hydroacylations. See refs. 20-24: Sakai K., Ishiguro Y., Funakoshi K., Ueno K., Suemune H., Tetrahedron Lett., 25, 961-964 (1984).
21. Taura Y., Tanaka M., Wu W.-M., Funakoshi K., Sakai K., Tetrahedron, 47, 4879-4888 (1991).
22. Tanaka M., Imai M., Fujio M., Sakamoto E., Takahashi M., Eto-Kato Y., Wu W.-M., Funakoshi K., Sakai K., Suemune H., J. Org. Chem., 65, 5806-5816 (2000).
23. Tanaka M., Takahashi M., Sakamoto E., Imai M., Matsui A., Fujio M., Funakoshi K., Sakai K., Suemune H., Tetrahedron, 57, 1197-1204 (2001).
24. Tanaka M., Sakai K., Suemune H., Cur. Org. Chem., 7, 353-367 (2003).
25. James B. R., Young C. G., J. Chem. Soc., Chem. Commun., 1983, 1215-1216 (1983).
26. Bosnich B., Acc. Chem. Res., 31, 667-674 (1998).
27. Tanaka K., Fu G. C., J. Am. Chem. Soc., 125, 8078-8079 (2003).
28. Tanaka K., J. Synth. Org. Chem. Jpn., 63, 351-358 (2005).
29. While we were studying an asymmetric intermolecular hydroacylation between salicylaldehyde and 1,5-hexadiene, Bolm et al., reported an unprecedented Rh-catalyzed asymmetric intermolecular hydroacylation of norbornadiene and norbornene. Also, Willis et al., reported the Rh-catalyzed asymmetric intermolecular hydroacylation of allenes. See refs. 30 and 31.
30. Stemmler R. T., Bolm C., Adv. Synth. Catal., 349, 1185-1198 (2007).
31. Osborne J. D., Randell-Sly H. E., Currie G. S., Cowley A. R., Willis M. C., J. Am. Chem. Soc., 130, 17232-17233 (2008).
32. Nozaki K., Sakai N., Nanno T., Higashijima T., Mano S., Horiuchi T., Takaya H., J. Am. Chem. Soc., 119, 4413-4423 (1997).
33. Breit B., Seiche W., Synthesis, 2001, 1-36 (2001).
34. Tanaka M., Imai M., Yamamoto Y., Tanaka K., Shimowatari M., Nagumo S., Kawahara N., Suemune H., Org. Lett., 5, 1365-1367 (2003).
35. Imai M., Tanaka M., Tanaka K., Yamamoto Y., Imai-Ogata N., Shimowatari M., Nagumo S., Kawahara N., Suemune H., J. Org. Chem., 69, 1144-1150 (2004).
36. Tanaka K., Tanaka M., Suemune H., Tetrahedron Lett., 46, 6053-6056 (2005).
37. Imai M., Tanaka M., Nagumo S., Kawahara N., Suemune H., J. Org. Chem., 72, 2543-2546 (2007).
38. 2Cl solution gave good results. See refs. 34-37.
39. The Rh-catalyzed asymmetric intermolecular hydroacylation of norbornene derivatives with salicylaldehyde was attempted under the same reaction conditions, but the hydroacylation did not proceed in the presence of Zn salts.