Reductive aldol-type reaction of α,β-unsaturated esters with aldehydes or ketones in the presence of Rh catalyst and Et2Zn

Tetrahedron Letters

Volumn 54, Issue 44, 2013, Pages 5913-5915

  Sato, Kazuyuki ^a   Isoda, Motoyuki ^a   Tokura, Yoriko ^a   Omura, Keiko ^a   Tarui, Atsushi ^a   Omote, Masaaki ^a   Kumadaki, Itsumaro ^a   Ando, Akira ^a  

^a SETSUNAN UNIVERSITY   (Japan)

Author keywords

Diethyl zinc; Reductive aldol reaction; Reformatsky Honda reaction; Rh H complex; RhCl(PPh 3)3

Indexed keywords

ALDEHYDE DERIVATIVE; ESTER DERIVATIVE; KETONE DERIVATIVE; RHODIUM DERIVATIVE;

ALDOL REACTION; ARTICLE; CATALYST; REDUCTION; REFORMATSKY REACTION; SYNTHESIS;

EID: 84884906862     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.08.109     Document Type: Article

References (25)

1. For Cu-catalyzed reductive aldol reactions: T. Ooi, K. Doda, D. Sakai, and K. Maruoka Tetrahedron Lett. 40 1999 2133 2136
2. H.W. Lam, and P.M.A. Joensuu Org. Lett. 7 2005 4225 4228
3. A. Welle, S. Díez-González, B. Tinant, S.P. Nolan, and O. Riant Org. Lett. 8 2006 6059 6062
4. For Co-catalyzed reductive aldol reactions: S. Isayama, and T. Mukaiyama Chem. Lett. 1989 2005 2008
5. T.G. Baik, A.L. Luis, L.C. Wang, and M.J. Krische J. Am. Chem. Soc. 123 2001 5112 5113
6. L.C. Wang, H.-Y. Jang, Y. Roh, V. Lynch, A.J. Schultz, X. Wang, and M.J. Krische J. Am. Chem. Soc. 124 2002 9448 9453
7. H.W. Lam, P.M. Joensuu, G.J. Murray, E.A.F. Fordyce, O. Prieto, and T. Luebbers Org. Lett. 8 2006 3729 3732
8. R.J.R. Lumby, P.M. Joensuu, and H.W. Lam Org. Lett. 9 2007 4367 4370
9. For Rh-catalyzed reductive aldol reactions: A. Revis, and T.K. Hilty Tetrahedron Lett. 28 1987 4809 4812
10. H. Nishiyama, T. Shiomi, Y. Tsuchiya, and I. Matsuda J. Am. Chem. Soc. 127 2005 6972 6973
11. M.C. Willis, and R.L. Woodward J. Am. Chem. Soc. 127 2005 18012 18013
12. C. Bee, S.B. Han, A. Hassan, H. Iida, and M.J. Krische J. Am. Chem. Soc. 130 2008 2746 2747
13. T. Hashimoto, J. Ito, and H. Nishiyama Tetrahedron 64 2008 9408 9412
14. T. Shiomi, T. Adachi, J. Ito, and H. Nishiyama Org. Lett. 11 2009 1011 1014
15. For intermolecular reductive aldol reactions with ketones: D. Zhao, K. Oisaki, M. Kanai, and M. Shibasaki Tetrahedron Lett. 47 2006 1403 1407
16. J. Deschamp, O. Chuzel, J. Hannedouche, and O. Riant Angew. Chem., Int. Ed. 45 2006 1292 1297
17. T. Shiomi, and H. Nishiyama Org. Lett. 9 2007 1651 1654
18. R.J.R. Lumby, P.M. Joensuu, and H.W. Lam Tetrahedron 64 2008 7729 7740
19. M. Kato, H. Oki, K. Ogata, and S. Fukuzawa Synlett 2009 1299 1302
20. K. Sato, S. Yamazoe, R. Yamamoto, S. Ohata, A. Traui, M. Omote, A. Ando, and I. Kumadaki Org. Lett. 10 2008 2405 2408
21. K. Sato, M. Isoda, S. Ohata, S. Morita, A. Tarui, M. Omote, I. Kumadaki, and A. Ando Adv. Synth. Catal. 354 2012 510 514
22. K. Kanai, H. Wakabayashi, and T. Honda Org. Lett. 2 2000 2549 2551
23. K. Kanai, H. Wakabayashi, and T. Honda Heterocycles 58 2002 47 51
24. T. Honda, H. Wakabayashi, and K. Kanai Chem. Pharm. Bull. 50 2002 307 308
25. K. Sato, Y. Ishida, E. Murata, Y. Oida, Y. Mori, M. Okawa, K. Iwase, A. Tarui, M. Omote, I. Kumadaki, and A. Ando Tetrahedron 63 2007 12735 12739