Catalyzed acyl halide-aldehyde cyclocondensations. New insights into the design of catalytic cross aldol reactions

Tetrahedron Letters

Volumn 40, Issue 36, 1999, Pages 6535-6539

  Nelson, Scott G ^a   Wan, Zhonghui ^a   Peelen, Timothy J ^a   Spencer, Keith L ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 PROPANOL; ACID HALIDE; ALDEHYDE; ALUMINUM DERIVATIVE; ANTIMONY DERIVATIVE; DIETHYLAMINE; FLUORINE DERIVATIVE; LACTONE DERIVATIVE;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; CYCLIZATION; STEREOSPECIFICITY; STOICHIOMETRY;

EID: 0033520215     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01308-8     Document Type: Article

References (22)

1. For a review of catalyzed aldol reactions involving latent enolate equivalents, see: Nelson, S. G. Tetrahedron: Asymmetry 1998, 9, 357-389.
2. For a recent report of catalyzed intermolecular aldol reactions, see: (a) Yoshikawa, N.; Yamada, Y. M. A.; Das, J.; Sasai, H.; Shibasaki, M. J. Am. Chem. Soc. 1999, 121, 4168-4178.
3. For other recent examples of reactions involving catalytic enolization, see: (b) Shibasaki, M.; Sasi, H.; Arai, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1236-1256, and references cited therein.
4. Evans, D. A.; Nelson, S. G. J. Am. Chem. Soc. 1997, 119, 6452-6453.
5. Ito, Y.; Sawamura, M.; Hayashi, T. J. Am. Chem. Soc. 1986, 108, 6405-6406.
6. For a comprehensive review of β-lactone syntheses via ketene-aldehyde cycloadditions, see: Hyatt, J. A.; Raynolds, P. W. Org. Reacts. (Ny) 1994, 45, 159-646.
7. For recent advances in β-lactone synthesis, see: (b) Calter, M. A. J. Org. Chem. 1996, 61, 8006-8007.
8. Dymock, B. W.; Kocienski, P. J.; Pons, J.-M. J. Chem. Soc., Chem. Commun. 1996, 1053-1054.
9. Romo, D.; Harrison, P. H. M.; Jenkins, S. I.; Riddoch, R. W.; Park, K.; Yang, H. W.; Zhao, C.; Wright, G. D. Bioorg. Med. Chem. 1998, 6, 1255-1272, and references cited therein.
10. For a review of transformations involving β-lactones, see: Pommier, A.; Pons, J.-M. Synthesis 1993, 441-459.
11. For methods of ketene generation, see Ref. a. Trimethylsilylketene is a commercially available substitute for gaseous ketene, see: (a) Brady, W. T.; Saidi, K. J. Org. Chem. 1979, 44, 733-737.
12. Maruoka, K.; Concepcion, A. B.; Yamamoto, H. Synlett 1992, 31-32 (see also Ref. 3d). However, the reagent is quite costly or must be prepared from expensive starting materials.
13. For a related Lewis acid-promoted acid chloride-aldehyde condensation employing dichloroacetyl chloride as the ketene precursor, see: Palomo, C.; Miranda, J. I.; Linden, A. J. Org. Chem. 1996, 61, 9196-9201.
14. Dioxanone is formally the :1 aldehyde:ketene addition product. Under the cyclocondensation reaction conditions, dioxanone and β-lactone do not interconvert, see: Nelson, S. G.; Peelen, T. J.; Wan, Z. Tetrahedron Lett. 1999, 40, 6541-6543.
15. Paukstelis, J. V.; Kim, M.-g. J. Org. Chem. 1974, 39, 1503-1507.
16. 6 stoichiometry (1:3) used to generate the catalyst complex; the structure of the resulting catalyst complex was not rigorously established.
17. 3.
18. 2 and the product was isolated by column chromatography (hexanes:ethyl acetate).
19. 13C NMR analysis of the crude reaction mixtures (≥95% purity). Under the optimized reaction conditions, no traces of aldehyde homoaldol products could be detected.
20. Reaction yields using 2.5 mol% catalyst are unoptimized.
21. 3N in refluxing methanol has also been reported, see; Koichi, Y.; Suginaka, K.; Yamamoto, Y. J. Chem. Soc., Perkin Trans. 1 1995, 1645-1646.
22. 1H NMR of crude reaction mixture.