Tandem conjugate reduction-aldol cyclization using stryker's reagent

Organic Letters

Volumn 3, Issue 12, 2001, Pages 1901-1903

  Chiu, Pauline ^a   Szeto, Chun Pong ^a   Geng, Zhe ^a   Cheng, Kin Fai ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

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EID: 0000975755     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015944n     Document Type: Article

References (34)

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8. (e) Taylor, S. J.; Morken, J. P. J. Am. Chem. Soc. 1999, 121, 12202. For a recent catalytic asymmetric reductive aldol, see:
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10. Some representative examples: (a) Ikeno, T.; Kimura, T.; Ohtsuka, Y.; Yamada, T. Synlett 1999, 96.
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14. (a) Mahoney, W. S.; Brestensky, D. M.; Stryker, J. M. J. Am. Chem. Soc. 1988, 110, 291.
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18. (c) Chen, J. X.; Daeuble, J. F.; Brestensky, D. M.; Stryker, J. M. Tetrahedron 2000, 56, 2153.
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24. There are very few studies of the preparation and chemistry of true copper enolates: (a) Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.4, p 99. One well-studied and particularly effective example: (b) Kruger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837.
25. There are very few studies of the preparation and chemistry of true copper enolates: (a) Mekelburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.4, p 99. One well-studied and particularly effective example: (b) Kruger, J.; Carreira, E. M. J. Am. Chem. Soc. 1998, 120, 837.
26. (c) Pagenkopf, B. L.; Kruger, J.; Stojanovic, A.; Carreira, E. M. Angew. Chem., Int. Ed. 1998, 37, 3124.
27. (a) Chiu, P.; Chen, B.; Cheng, K. F. Tetrahedron Lett. 1998, 39, 9229.
28. (b) For a case of a fragmentation to give a copper enolate that underwent an intramolecular aldol, see ref 6d. Other examples where the copper enolates from Stryker reduction were utilized synthetically:
29. (c) Alkylation: Koenig, T. M.; Daeuble, J. F.; Brestensky, D. M.; Stryker, J. M. Tetrahedron Lett. 1990, 31, 3237.
30. (d) O-Acylation: Raimundo, B. C.; Heathcock, C. H. Org. Lett. 2000, 2, 27.
31. (e) Michael addition: Kamenecka, T. M.; Ly, S. K.; Overman, L. E. Abstract of Papers, 212th National Meeting of the American Chemical Society, Orlando, FL; American Chemical Soceity: Washington, DC, 1996; ORGN 010. Ly, S. K. Ph.D. Dissertation, University of California, Irvine, CA, 1998.
32. 4Cl solution and stirring for 2 h open to air. Workup and purification by flash chromatography gave 3 (21.8 mg, 93%). For detailed experimental procedures, refer to Supporting Information.
33. For studies in the regioselectivity of base-induced intramolecular aldol reactions, see: Heathcock, C. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991; Vol. 2, Chapter 1.5, p 133.
34. The trans-fused hydroxyketone 4 (30.7799 kcal/mol) is slightly more stable thermodynamically than the cis-fused isomer 3 (30.9785 kcal/mol) by MM2 calculations (Macromodel v. 4.5 MacroModel3D). The structures of stereoisomers 3 and 4 have been determined on the basis of spectroscopic evidence; in addition, the structure of isomer 3 has been confirmed by X-ray crystallography of its 2,4-dinitrophenylhydrazone derivative.