Asymmetric synthesis of α-chiral dihydrocinnamates by catalytic reductive aldol coupling and subsequent dehydroxylation

Tetrahedron

Volumn 63, Issue 52, 2007, Pages 12883-12887

  Hashimoto, Toru ^a   Shiomi, Takushi ^a   Ito, Jun ichi ^a   Nishiyama, Hisao ^a  

^a NAGOYA UNIVERSITY   (Japan)

Author keywords

Asymmetric catalysis; Dihydrocinnamate; Reductive aldol; Rhodium

Indexed keywords

ACETONE; ACRYLIC ACID DERIVATIVE; ALDEHYDE DERIVATIVE; BENZALDEHYDE DERIVATIVE; CINNAMIC ACID DERIVATIVE; CROTONIC ACID DERIVATIVE; ESTER DERIVATIVE; RHODIUM;

ALDOL REACTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHIRALITY; CRYSTAL STRUCTURE; HYDROXYLATION; PRIORITY JOURNAL; REDUCTION; SYNTHESIS;

EID: 36148982239     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2007.10.055     Document Type: Article

References (14)

1. For examples of bioactive dihydrocinnamates: for renin inhibitors
2. Sturm T., Weissensteiner W., and Spindler F. Adv. Synth. Catal. 345 (2003) 160 For vitronectin receptor antagonists
3. Dondoni A., Lathauwer G.D., and Perrone D. Tetraheron Lett. 42 (2001) 4819 For γ-secretase inhibitors
4. Churcher I., Ashton K., Butcher J.W., Clarke E.E., Harrison H.D.L., Owens A.P., Teall M.R., Williams S., and Wrigley J.D. Bioorg. Med. Chem. Lett. 13 (2003) 179 For opioid antagonists
5. Lu Y., Nguyen T.M.D., Weltrowska G., Berezowska I., Lemieux C., Chung N.N., and Schiller P.W. J. Med. Chem. 44 (2001) 3048 For dihydrocinnamate as a building block
6. Chang L.L., Hannah J., Ashton W.T., Rasmusson G.H., Ikeler T.J., Patel G.F., Garsky V., Uncapher C., Yamanaka G., McClements W.L., and Tolman R.L. Bioorg. Med. Chem. Lett. 2 (1992) 1207
7. Hoen R., Booers J.A.F., Bernsmann H., Minnaard A.J., Meestsma A., Tiemersma-Wegman T.D., de Vries A.H.M., de Vries J.G., and Feringa B.L. Angew. Chem., Int. Ed. 44 (2005) 4209
8. Nishiyama H., Shiomi T., Tsuchiya Y., and Matsuda I. J. Am. Chem. Soc. 127 (2005) 6972
9. Ito J., Shiomi T., and Nishiyama H. Adv. Synth. Catal. 348 (2006) 1235
10. Shiomi T., and Nishiyama H. Org. Lett. 9 (2007) 1651
11. 2SiHCl was examined to give complicated products
12. Several reduction method such as hydrogenolysis with Pd/C and other silane-based reductions were examined to result in very low yields. Electron donating group such as MeO group on C is important to accelerate dehydroxylation process.
13. 2MeSiH was employed to decrease the ee for the syn-product; anti/syn=85:15, 83% ee for anti and 39% for syn.
14. Kanazawa Y., Tsuchiya Y., Kobayashi K., Shiomi T., Itoh J., Kikuchi M., Yamamoto Y., and Nishiyama H. Chem.-Eur. J. 12 (2006) 63