A solution to the cyclic aldol problem

Organic Letters

Volumn 2, Issue 9, 2000, Pages 1193-1196

  Baldwin, Steven W ^a   Chen, Ping ^a   Nikolic, Nikola ^a   Weinseimer, Daniel C ^a  

^a DUKE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001122974     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol005525a     Document Type: Article

References (45)

1. For comprehensive discussions of the various aspects of the aldol condensation see: (a) Meckleburger, H. B.; Wilcox, C. S. In Comprehensive Organic Synthesis; Trost B. M., Fleming, I., Eds.; Pergamon Press: Elmsford, NY, 1991; Vol. 2, pp 99-131.
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8. An excellent summary of pertinent literature and definitive physical organic studies of the aldol reaction can be found in: Arnett, E. M.; Fisher, F. J.; Nichols, M. A.; Ribiero, A. A. J. Am. Chem. Soc. 1990, 112, 801.
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38. 2, and TMSOTf, although the diastereomeric ratios with these promoters were generally lower.
39. 1H NMR spectroscopy. In the latter analyses, the quartet for the proton on the hydroxyl-bearing carbon was diagnostic, occurring between 0.1 and 0.2 ppm downfield in the syn isomers as compared to the anti isomers (e.g., δ 4.08 and δ 3.98 for 7syn and 7anti, respectively).
40. Snider, B. B.; Patricia, J. J. J. Org. Chem. 1989, 54, 38.
41. For a discussion of intramolecular nitrile oxide/alkene cycloaddition (INOC) reactions, see: Wade, P. A. In Comprehensive Organic Synthesis; Trost B. M., Fleming, I., Eds.; Pergamon Press: Elmsford, NY, 1991; Vol. 4, pp 1124-1134.
42. Curran, D. P. J. Am. Chem. Soc. 1983, 105, 5826.
43. Hudlicky, T.; Sinai-Zingde, G.; Natchus, M. G. Tetrahedron Lett. 1987, 28, 5287.
44. The phenyl-substituted allylic alcohol precursors to epoxides 14 were prepared by lithiation of (Z)-1-bromo-1-phenylpropene followed by addition to cyclopentanone. At -78°C the Z/E ratio of the stereoisomeric products was ∼4/1; at -22°C the ratio was ∼1/4. Krop, P. J.; Crawford, S. D. J. Org. Chem. 1994, 59, 3102.
45. 13C NMR analysis and IR where appropriate. Suitably purified samples also exhibited consistent combustion analyses and/or high-resolution mass spectral data.