Synthesis of trifluoromethylated compounds with four consecutive asymmetric centers via sequential [3,3]-Ireland-Claisen rearrangement and iodolactonization

Tetrahedron Asymmetry

Volumn 8, Issue 2, 1997, Pages 223-230

  Konno, Tsutomu ^a   Kitazume, Tomoya ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID DERIVATIVE;

ARTICLE; CHEMICAL REACTION; COLUMN CHROMATOGRAPHY; DRUG SYNTHESIS; ENANTIOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031036747     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(96)00492-2     Document Type: Article

References (22)

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5. To the best of our knowledge, there is only one report concerning the synthesis of 1. However, 1 in the following report is not considered to be an useful chiral unit because the functionalities included in it could not be chemically distinguished. Lavaire, S.; Plantier-Royon, R.; Portella, C. J. Carbohydr. Chem. 1996, 15, 361.
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12. (c) Bartlett, P. A.; Myerson, J. J. Am. Chem. Soc. 1978, 100, 3950.
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15. (f) Dowle, M. D.; Davies, D. I. Chem. Soc. Rev. 1979, 171.
16. (a) Singh, H. S. In Organic Synthesis by Oxidation with Metal Compounds, Mijs, W. J., Dejong, R. H. I., Eds; Plemium Press, New York, 1986, Chapter 12.
17. (b) Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3943.
18. (c) Cha, J. K.; Christ, W. J.; Kishi, Y. Tetrahedron Lett. 1983, 24, 3947.
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20. Calculations were performed by MOPAC v 6.10 (AM1) implemented in CAChe Worksystem (SONY/Tektronix Corporation). The obtained conformers were verified as the real TSs not only by their force calculation giving only one imaginary frequencies, but also by the intrinsic reaction coordinate calculation affording the corresponding substrates and products.
21. 3 group is considered to be sterically similar to an isopropyl group. Bott, G.; Field, L. G.; Sternhell, S. J. Am. Chem. Soc. 1980, 102, 5618.
22. Kobayashi and coworkers have reported that in the iodolactonization of α-(phenylsulfenyl)-β-trifluoromethyl-γ,δ-unsaturated carboxylic acid derivative, syn isomer afforded the γ-lactone highly stereoselectively, while the reaction of anti isomer did not proceed at all. Hanzawa, Y.; Kawagoe, K.; Kawada, K.; Kobayashi, Y. Chem. Pharm. Bull. 1985, 33, 2579.