Convenient Wacker oxidations with substoichiometric cupric acetate

Tetrahedron Letters

Volumn 39, Issue 48, 1998, Pages 8765-8768

  Smith III, Amos B ^a   Cho, Young Shin ^a   Friestad, Gregory K ^a  

^a UNIVERSITY OF PENNSYLVANIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETONE; ALKENE; COPPER ACETATE;

ARTICLE; CHEMICAL MODIFICATION; HYDROLYSIS; OXIDATION REDUCTION REACTION; STOICHIOMETRY; SYNTHESIS;

EID: 0032569909     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01992-3     Document Type: Article

References (16)

1. 1. a) For a review, see: Tsuji, J. Synthesis 1984, 369.
2. b) For an application to synthesis of pseudomonic acid C, see: Balog, A.; Yu, M. S.; Curran, D. P.; Yu, G.; Carcanague, D. R.; Shue, Y.-K. Synthetic Commun. 1996, 26, 935.
3. c) For an application to synthesis of swinholides, see Paterson, I.; Cumming, J. G.; Smith, J. D.; Ward, R. A.; Yeung, K.-S. Tetrahedron Lett. 1994, 35, 3405.
4. d) For other recent synthetic applications, see Pellissier, H.; Michellys, P.-Y.; Santelli, M. Tetrahedron Lett. 1994, 35, 6481; Money, T.; Wong, M. K. C.Tetrahedron 1996, 6307.
5. d) For other recent synthetic applications, see Pellissier, H.; Michellys, P.-Y.; Santelli, M. Tetrahedron Lett. 1994, 35, 6481; Money, T.; Wong, M. K. C.Tetrahedron 1996, 6307.
6. 2. Smith, A. B., III; Friestad, G. K.; Duan, J. J.-W., Barbosa, J.; Hull, K. G.; Iwashima, M.; Qiu, Y.; Spoors, P. G.; Salvatore, B. A. J. Am. Chem. Soc., submitted.
7. 3. Roush, W. R.; Palkowitz, A. D.; Ando, K. J. Am. Chem. Soc. 1990, 112, 6348.
8. 13C NMR spectra, as well as appropriate parent ion identification by high resolution mass spectrometry.
9. 5. Tsuji, J.; Nagashima, H.; Nemoto, H. Org. Synth., Coll. Vol. 7 1990, 137.
10. 1H NMR properties consistent with hemiketal I. (equation presented)
11. 7. Cupric acetate has been empoyed in industrial Wacker oxidation, see: Hrusovsky, M.; Vojtko, J.; Cihova, M. Hung. J. Ind. Chem. 1974, 2, 137; Chemical Abstracts 1975, 82, 139205.
12. 7. Cupric acetate has been empoyed in industrial Wacker oxidation, see: Hrusovsky, M.; Vojtko, J.; Cihova, M. Hung. J. Ind. Chem. 1974, 2, 137; Chemical Abstracts 1975, 82, 139205.
13. 2 leads to chlorinated byproducts, see reference 1a.
14. 9. Molander, G. A.; Cameron, K. O. J. Org. Chem. 1993, 58, 5931.
15. 10. Alternate mechanisms may intervene in the oxidations of allylic alcohols and acetates.
16. 4, and concentrated. Adsorption on silica gel and gradient flash chromatography (hexanes → 3:1 hexanes/ethyl acetate) afforded 4 (1.68 g, 84.0% yield).