The direct aldol reaction using bifunctional catalysts

Tetrahedron Letters

Volumn 44, Issue 30, 2003, Pages 5699-5701

  Calter, Michael A ^a   Orr, Robert K ^a  

^a UNIVERSITY OF ROCHESTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; AMINE; BASE; BENZALDEHYDE DERIVATIVE; FUNCTIONAL GROUP; LEWIS ACID; ZINC;

ALDOL REACTION; ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; ENANTIOSELECTIVITY; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0037491396     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01332-7     Document Type: Article

References (21)

1. For recent advances in the direct aldol reaction, see: Lalic, G. L.; Aloise, A. D.; Shair, M. D. J. Am. Chem. Soc. 2003, 125, 2852-2853; (b) Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167-8177.
2. For recent advances in the direct aldol reaction, see: Lalic, G. L.; Aloise, A. D.; Shair, M. D. J. Am. Chem. Soc. 2003, 125, 2852-2853; (b) Nakadai, M.; Saito, S.; Yamamoto, H. Tetrahedron 2002, 58, 8167-8177.
3. List B., Lerner R.A., Barbas C.F. III. J. Am. Chem. Soc. 122:2000;2395-2396.
4. Notz W., List B. J. Am. Chem. Soc. 122:2000;7386-7387.
5. Hoang L., Bahmanyar S., Houk K.N., List B. J. Am. Chem. Soc. 125:2003;16-17.
6. Northrup A.B., MacMillan D.W.C. J. Am. Chem. Soc. 124:2002;6798-6799.
7. Yoshikawa N., Yamada Y.M.A., Das J., Sasai H., Shibasaki M. J. Am. Chem. Soc. 121:1999;4168-4178.
8. Kumagai N., Matasunaga S., Kinoshita T., Harada S., Okada S., Sakamoto S., Yamaguchi K., Shibasaki M. J. Am. Chem. Soc. 125:2003;2169-2178.
9. Trost B.M., Ito H. J. Am. Chem. Soc. 122:2000;12003-12004.
10. Trost B.M., Ito H., Silcoff E.R. J. Am. Chem. Soc. 123:2001;3367-3368.
11. Dreyer M.K., Schulz G.E. J. Mol. Biol. 1996;458-466.
12. Nakagawa M., Nakao H., Watanabe K. Chem. Lett. 1985;391-394.
13. Watanabe K., Yamada Y., Goto K. Bull. Chem. Soc. Jpn. 55:1985;1401-1406.
14. Yumada Y., Watanabe K., Yasuda H. Usonomiya Daiguku Kyoikugabubu Kiyo. 39:1989;25-31.
15. Ito Y., Sawamura M., Hayashi T. J. Am. Chem. Soc. 108:1986;6405-6406.
16. 1H NMR of concentrated aliquots.
17. Fry F.H., Fallon G.D., Spiccia L. Inorg. Chim. Acta. 2003;57-66.
18. Zoltan K., Sherry A.D. Tetrahedron Lett. 36:1995;9269-9272.
19. 2. The organic extract was concentrated and chromatographed (silica gel, EtOAc/hexanes) to yield the N,N-BOC,Me-amino acids.
20. 2 and EtOAc. The combined organic washes were evaporated to give the tetramines, which were used directly in the aldol reaction.
21. All new compounds gave satisfactory analytical and spectral data.