Mixed crossed aldol condensation between conjugated esters and aldehydes using aluminum tris(2,6-diphenylphenoxide)

Angewandte Chemie - International Edition

Volumn 38, Issue 12, 1999, Pages 1769-1771

  Saito, Susumu ^a   Shiozawa, Masahito ^a   Yamamoto, Hisashi ^a  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

Aldol reactions; C C coupling; Cross coupling; Enols

Indexed keywords

2,2,6,6 TETRAMETHYLPIPERIDIDE; ALDEHYDE; ALUMINUM DERIVATIVE; ALUMINUM TRIS(2,6 DIPHENYLPHENOXIDE); BENZALDEHYDE; ESTER; LITHIUM DERIVATIVE; OXIDE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION; CHEMICAL STRUCTURE; DIASTEREOISOMER; MOLECULAR MODEL; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0033553845     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990614)38:12<1769::AID-ANIE1769>3.0.CO;2-0     Document Type: Article

References (28)

1. a) O. H. House in Modern Synthetic Reactions (Ed.: R. Breslow), Benjamin, Menlo Park, NJ, USA, 1972, chap. 10, and references therein;
2. b) C. H. Heathcock in Comprehensive Organic Synthesis, Vol. 2 (Eds.: B. M. Trost, I. Fleming, C. H. Heathcock), Pergamon, Oxford, 1991, chap. 1.5, and references therein;
3. c) C. H. Heathcock in Modern Synthetic Methods 1992, Vol. 6 (Ed.: R. Scheffold), VHCA, Basel, 1992, chap. 1, and references therein.
4. S. Saito, M. Shiozawa, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1998, 120, 813.
5. For a general review of bulky aluminum reagents, including ATPH, see: S. Saito, H. Yamamoto, Chem. Commun. 1997, 1585.
6. 3Al (1 equiv) in hexane at room temperature under argon. The resulting pale yellow solution was stirred at this temperature for 30 min and used without further purification. a) S. Saito, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1997, 119, 611;
7. b) T. Ooi, K. Hokke, K. Maruoka, Angew. Chem. 1997, 109, 1230;
8. Angew. Chem. Int. Ed. Engl. 1997, 36, 1181;
9. c) K. Maruoka, M. Ito, H. Yamamoto, J. Am. Chem. Soc. 1995, 117, 9091;
10. d) K. Maruoka, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1995, 117, 1165;
11. e) K. Maruoka, H. Imoto, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 12115;
12. f) K. Maruoka, H. Imoto, S. Saito, H. Yamamoto, J. Am. Chem. Soc. 1994, 116, 4131.
13. With the exception of our case, the extended dienolates of esters are invariably prone to α-functionalization: a) D. Caine in Comprehensive Organic Synthesis, Vol. 3 (Eds.: B. M. Trost, I. Fleming, G. Pattenden), Pergamon, Oxford, 1991, chap. 1.1, and references therein;
14. b) S. Saito, H. Yamamoto, Chem. Eur. J., in press.
15. Preparation of 5: a) H. O. House, V. K. Jones, G. A. Frank, J. Org. Chem. 1964, 29, 3327.
16. Highly conjugated esters 8-11 were prepared as described in the literature, through a Horner-Emmons olefination with diethyl phosphonoacetic acid ethyl ester (methyl ester for 8): b) M. Bellassoued, A. Majidi, J. Org. Chem. 1993, 58, 2517.
17. a) P. Wipf, P. D. G. Coish, Tetrahedron Lett. 1997, 38, 5073;
18. b) B. H. Lipshutz, C. Lindsley, J. Am. Chem. Soc. 1997, 119, 4555;
19. c) J. Thibonnet, M. Abarbi, J. L. Parrain, A. Duchêne, Synlett 1997, 771;
20. d) D. Boschelli, T. Takemasa, Y. Nishitani, S. Masamune, Tetrahedron Lett. 1985, 26, 5239.
21. There are many examples of δ-hydroxy-α,β-unsaturated esters and their related units involved in the synthesis of important natural products: a) X. Fan, G. R. Flentke, D. H. Rich, J. Am. Chem. Soc. 1998, 120, 8893;
22. b) T. I. Richardson, S. D. Rychnovsky, J. Am. Chem. Soc. 1997, 119, 12360;
23. c) A. B. Smith III, G. R. Ott, J. Am. Chem. Soc. 1996, 118, 13095;
24. d) C. S. Poss, S. D. Rychnovsky, S. L. Schreiber, J. Am. Chem. Soc. 1993, 115, 3360;
25. e) G. E. Keck, J. A. Murry, J. Org. Chem. 1991, 56, 6606;
26. f) K. C. Nicolaou, T. K. Chakraborty, Y. Ogawa, R. A. Daines, N. S. Simpkins, G. T. Furst, J. Am. Chem. Soc. 1988, 110, 4660;
27. g) K. C. Nicolaou, R. A. Daines, T. K. Chakraborty, Y. Ogawa, J. Am. Chem. Soc. 1988, 110, 4685.
28. P. R. Johnson, J. D. White, J. Org. Chem. 1984, 49, 4424.