Catalytic Asymmetric Acyl Halide-Aldehyde Cyclocondensation Reactions of Substituted Ketenes

Journal of the American Chemical Society

Volumn 126, Issue 1, 2004, Pages 14-15

  Nelson, Scott G ^a   Zhu, Cheng ^a   Shen, Xiaoqiang ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACID HALIDE; ALDEHYDE; INORGANIC SALT; KETENE DERIVATIVE; LACTONE DERIVATIVE; LEWIS ACID; SOLVENT;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CYCLOCONDENSATION REACTION; DIASTEREOISOMER; ENANTIOMER; GEOMETRY; LOW TEMPERATURE; POLYMERIZATION; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; TEMPERATURE SENSITIVITY;

EID: 0347129844     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0391208     Document Type: Article

References (25)

1. For excellent reviews: (a) Yang, H. W.; Romo, D. Tetrahedron 1999, 55, 6403.
2. (b) Orr, R. K.; Calter, M. A. Tetrahedron 2003, 59, 3545.
3. Leading references to catalytic asymmetric β-lactone preparation: (a) Wynberg, H.; Staring, E. G. J. J. Am. Chem. Soc. 1982, 104, 166.
4. (b) 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.
5. (c) Nelson, S. G.; Peelen, T. J.; Wan, Z. J. Am. Chem. Soc. 1999, 121, 9742.
6. (d) Nelson, S. G.; Wan, Z. Org. Lett. 2000, 2, 1883.
7. (e) Tennyson, R.; Romo, D. J. Org. Chem. 2000, 65, 7248.
8. (f) Evans, D. A.; Janey, J. M. Org. Lett. 2001, 3, 2125.
9. (g) Cortez, G. S.; Tennyson, R. L.; Romo, D. J. Am. Chem. Soc. 2001, 123, 7945.
10. (h) Calter, M. A.; Liao, W. J. Am. Chem. Soc. 2002, 124, 13127 and references therein.
11. Nelson, S. G.; Spencer, K. L. Angew. Chem., Int. Ed. 2000, 39, 1323.
12. Wan, Z.; Nelson, S. G. J. Am. Chem. Soc. 2000, 122, 10470.
13. Nelson, S. G.; Wan, Z.; Stan, M. A. J. Org. Chem. 2002, 67, 4680.
14. Nelson, S. G.; Wan, Z.; Peelen, T. J.; Spencer, K. L. Tetrahedron Lett. 1999, 40, 6535.
15. For examples of direct catalytic asymmetric ester enolate aldols, see: (a) Juhl, K.; Gathergood, N.; Jørgensen, K. A. Chem. Commun. 2000, 2211.
16. (b) Taylor, S. J.; Duffey, M. O.; Morken, J. P. J. Am. Chem. Soc. 2000, 122, 4528.
17. See also: (c) Evans, D. A.; Tedrow, J. S.; Shaw, J. T.; Downey, C. W. J. Am. Chem. Soc. 2002, 124, 392.
18. AAC reactions involving substituted ketenes had previously been applicable only to a very limited subset of activated aldehydes: see ref 2d.
19. Nelson, S. G.; Peelen, T. J.; Wan, Z. Tetrahedron Lett. 1999, 40, 6541.
20. Ketene trimerization is accelerated considerably for substituted ketenes relative to unsubstituted ketene under the AAC reaction conditions.
21. Ogawa, A.; Curran, D. P. J. Org. Chem. 1997, 62, 450.
22. Nelson, S. G.; Kim, B.-K.; Peelen, T. J. J. Am. Chem. Soc. 2000, 122, 9318.
23. Ligands having a central nitrogen atom devoid of Lewis basicity (noncoordinating) afford catalytically inactive Al(III) complexes: see ref 12.
24. 2 groups have been omitted from Figure 1 for clarity.
25. α-Branched aldehydes and conjugated enals are not effective substrates for the AAC reactions, affording substantially attenuated enantioselection (60-70% ee) or no reaction, respectively.