Asymmetric vinylogous direct aldol reaction using aluminum tris[2,6-bis(4-alkylphenyl)phenoxide]

Synlett

Volumn , Issue 4, 2004, Pages 732-734

  Takikawa, Hiroshi ^a   Ishihara, Kazuaki ^a   Saito, Susumu ^a   Yamamoto, Hisashi ^b  

^a NAGOYA UNIVERSITY   (Japan)

^b UNIVERSITY OF CHICAGO   (United States)

Author keywords

Aldol reactions; Aluminum; Asymmetric synthesis; Chiral auxiliaries; Host guest systems

Indexed keywords

ALDEHYDE DERIVATIVE; ALUMINUM DERIVATIVE; ESTER DERIVATIVE; PROTON; VINYL DERIVATIVE;

ALDOL REACTION; ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHIRALITY; COMPLEX FORMATION; CONFORMATIONAL TRANSITION; DIASTEREOISOMER; ENANTIOMER; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; TECHNIQUE;

EID: 1642389115     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-817761     Document Type: Article

References (24)

1. (a) Casiraghi, G.; Zanardi, F.; Battistini, L.; Appendino, G. Chemtracts 1999, 12, 547.
2. (b) Saito, S.; Yamamoto, H. Chem.-Eur. J. 1999, 5, 1959.
3. (c) Casiraghi, G.; Zanardi, F.; Battistini, L.; Appendino, G.; Rassu, G. Chem. Rev. 2000, 100, 1929.
4. (a) Paterson, I.; Smith, J. D. J. Org. Chem. 1992, 57, 3261.
5. (b) Cahard, D.; Poirier, J.-M.; Duhamel, P. Tetrahedron Lett. 1998, 39, 7093.
6. (c) ATPH was used in the synthesis of Callipeltoside Aglycon, see:Paterson, I.; Davies, R. D. M.; Marquez, R. Angew. Chem. Int. Ed. 2001, 40, 603.
7. (d) The dienolates of γ-or β-heteroatom-substituted α,β-unsaturated carbonyl compounds are prone to vinylogous aldol reaction, see:Krüger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837.
8. (e) See also:Rassu, G.; Pinna, L.; Spanu, P.; Zanardi, F.; Battistini, L.; Casiraghi, G. J. Org. Chem. 1997, 62, 4513.
9. (f) See also ref. 1
10. (a) Bluet, G.; Campagne, J.-M. Tetrahedron Lett. 1999, 40, 5507.
11. (b) Bluet, G.; Campagne, J.-M. J. Org. Chem. 2001, 66, 4293.
12. (a) Saito, S.; Shiozawa, M.; Nagahara, T.; Nakadai, M.; Yamamoto, H. J. Am. Chem. Soc. 2000, 122, 7847.
13. (b) Saito, S.; Shiozawa, M.; Yamamoto, H. Angew. Chem. Int. Ed. 1999, 38, 1769.
14. (c) Saito, S.; Ito, M.; Shiozawa, M.; Yamamoto, H. J. Am. Chem. Soc. 1998, 120, 813.
15. (d) Saito, S.; Yamazaki, S.; Yamamoto, H. Angew. Chem. Int. Ed. 2001, 40, 3613.
16. (e) Saito, S.; Sone, T.; Murase, M.; Yamamoto, H. J. Am. Chem. Soc. 2000, 122, 10216.
17. (f) For detailed mechanistic aspects of the present vinylogous aldol reaction, see: Saito, S.; Nagahara, H.; Shiozawa, M.; Nakadai, M.; Yamamoto, H. J. Am. Chem. Soc. 2003, 125, 6200.
18. (g) For a review of ATPH, see: Saito, S.; Yamamoto, H. Chem. Commun. 1997, 1585.
19. Me-ATPH was prepared by the procedure similar to ATPH. The corresponding phenol was prepared via four steps from commercial 2,6-dibromophenol. For experimental details, see the forthcoming paper: Ito, H.; Nagahara, T.; Ishihara, K.; Saito, S.; Yamamoto, H. Angew. Chem. Int. Ed. 2004, in press.
20. The use of a less amount of the ester, ATPH, and LTMP (1.0:2.2:1.2 equiv) proved less productive. See also ref. 4b
21. 3.
22. Significant effects of second equivalent of ATPH, which presumably activates the aldehyde partner, needs further investigation. In the absence of the second ATPH, considerable decrease in chemical yields was consistently observed.
23. 3-symmetry in chiral recognition, see:Moberg, C. Angew. Chem. Int. Ed. 1998, 37, 248.
24. 8): δ = 7.70-6.50 (m, 39 H), 5.99 (qd, J = 7.2, 25.4 Hz, 1 H), 4.76 (d, J = 25.6 Hz, 1 H), 3.66 (m, 1 H), 2.05 (s, 18 H), 1.68 (br s, 1 H), 1.36 (m, 2 H), 1.20 (br d, J = 11.7 Hz), 0.93 (d, J = 6.9 Hz, 3 H), 0.78 (d, J = 6.9 Hz, 3 H), 0.64 (d, J = 6.9 Hz, 3 H), 0.60 (d, J = 6.0 Hz, 3 H), 1.15-0.56 (m, 4 H), 0.50 (br d, J = 11.7 Hz, 1 H). The Me-ATPH-2a complex is highly likely to adopt a most favorable diastereomeric conformation with a negligible formation of other distinct diastereomers. See also ref. 5 for the X-ray single crystal structure of a homochiral ester complex of ATPH.