Sc(OTf)3- and TfOH-catalyzed Baeyer-Villiger oxidation of carbonyl compounds with m-chloroperbenzoic acid

Synlett

Volumn , Issue 4, 1999, Pages 462-464

  Kotsuki, Hiyoshizo ^a   Arimura, Koji ^a   Araki, Tomohiro ^a   Shinohara, Toshio ^a  

^a KOCHI UNIVERSITY   (Japan)

Author keywords

Baeyer Villger oxidation; M CPBA; Sc(OTf)3; TfOH

Indexed keywords

3 CHLOROPERBENZOIC ACID; BENZOIC ACID DERIVATIVE; CARBONYL DERIVATIVE; ESTER; HYDROGEN PEROXIDE; LACTONE; MESYLIC ACID DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; UNCLASSIFIED DRUG;

ACCELERATION; ARTICLE; CATALYSIS; CHEMICAL BOND; CHEMICAL PROCEDURES; CHEMICAL REACTION; OXIDATION; REACTION TIME;

EID: 0032944506     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2648     Document Type: Article

References (38)

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19. Reviews: Kobayashi, S. Synlett 1994, 689-701; Kobayashi, S. J. Synth. Org. Chem. Jpn. 1995, 53, 370-380; Marshman, R. W. Aldrichimica Acta 1995, 28, 77-84; Kobayashi, S. J. Synth. Org. Chem. Jpn. 1998, 56, 357-367.
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23. The use of less amounts of m-CPBA led invariably to incomplete reactions.
24. 3-catalyzed reactions. The recycled use of the catalyst was fruitless due to the tedious purification after workup procedure.
25. In this case strictly anhydrous conditions were necessary to achieve enough activity.
26. pKa value of TfOH is <-11: Hendrickson, J. B.; Sternbach, D. D.; Bair, K. W. Acc. Chem. Res., 1977, 10, 306-312.
27. Satisfactory spectral data were obtained for all new compounds.
28. Schultz, A. G.; Pettus, L. J. Org. Chem. 1997, 62, 6855-6861 and references cited therein.
29. Unavoidable hydrolysis of 2-naphthyl formate was observed during Chromatographic purification.
30. See for example, Toda, F.; Yagi, M.; Kiyoshige, K. J. Chem. Soc., Chem. Commun. 1988, 958-959; Fringuelli, F.; Germani, R.; Pizzo, F.; Savelli, G. Gazz. Chim. Ital. 1989, 119, 249.
31. See for example, Toda, F.; Yagi, M.; Kiyoshige, K. J. Chem. Soc., Chem. Commun. 1988, 958-959; Fringuelli, F.; Germani, R.; Pizzo, F.; Savelli, G. Gazz. Chim. Ital. 1989, 119, 249.
32. For some recent examples of asymmetric Baeyer-Villiger oxidation, see: Bolm, C.; Schlingloff, G.; Weickhardt, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 1848-1849; Gusso, A.; Baccin, C.; Pinna, F.; Strukul, G. Organometallics 1994, 13, 3442-3451; Bolm, C.; Schlingloff, G. J. Chem. Soc., Chem. Commun. 1995, 1247-1248; Lopp, M.; Paju, A.; Kanger, T.; Pehk, T. Tetrahedron Lett. 1996, 37, 7583-7586; Bolm, C.; Schlingloff, G.; Bienewald, F. J. Mol. Catal. 1997, 117, 347-350; Strukul, G.; Varagnolo, A.; Pinna, F. ibid. 1997, 117, 413-423; Bolm, C.; Luong, T. K. K.; Schlingloff, G. Synlett 1997, 1151-1152. See also Ref. 7.
33. For some recent examples of asymmetric Baeyer-Villiger oxidation, see: Bolm, C.; Schlingloff, G.; Weickhardt, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 1848-1849; Gusso, A.; Baccin, C.; Pinna, F.; Strukul, G. Organometallics 1994, 13, 3442-3451; Bolm, C.; Schlingloff, G. J. Chem. Soc., Chem. Commun. 1995, 1247-1248; Lopp, M.; Paju, A.; Kanger, T.; Pehk, T. Tetrahedron Lett. 1996, 37, 7583-7586; Bolm, C.; Schlingloff, G.; Bienewald, F. J. Mol. Catal. 1997, 117, 347-350; Strukul, G.; Varagnolo, A.; Pinna, F. ibid. 1997, 117, 413-423; Bolm, C.; Luong, T. K. K.; Schlingloff, G. Synlett 1997, 1151-1152. See also Ref. 7.
34. For some recent examples of asymmetric Baeyer-Villiger oxidation, see: Bolm, C.; Schlingloff, G.; Weickhardt, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 1848-1849; Gusso, A.; Baccin, C.; Pinna, F.; Strukul, G. Organometallics 1994, 13, 3442-3451; Bolm, C.; Schlingloff, G. J. Chem. Soc., Chem. Commun. 1995, 1247-1248; Lopp, M.; Paju, A.; Kanger, T.; Pehk, T. Tetrahedron Lett. 1996, 37, 7583-7586; Bolm, C.; Schlingloff, G.; Bienewald, F. J. Mol. Catal. 1997, 117, 347-350; Strukul, G.; Varagnolo, A.; Pinna, F. ibid. 1997, 117, 413-423; Bolm, C.; Luong, T. K. K.; Schlingloff, G. Synlett 1997, 1151-1152. See also Ref. 7.
35. For some recent examples of asymmetric Baeyer-Villiger oxidation, see: Bolm, C.; Schlingloff, G.; Weickhardt, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 1848-1849; Gusso, A.; Baccin, C.; Pinna, F.; Strukul, G. Organometallics 1994, 13, 3442-3451; Bolm, C.; Schlingloff, G. J. Chem. Soc., Chem. Commun. 1995, 1247-1248; Lopp, M.; Paju, A.; Kanger, T.; Pehk, T. Tetrahedron Lett. 1996, 37, 7583-7586; Bolm, C.; Schlingloff, G.; Bienewald, F. J. Mol. Catal. 1997, 117, 347-350; Strukul, G.; Varagnolo, A.; Pinna, F. ibid. 1997, 117, 413-423; Bolm, C.; Luong, T. K. K.; Schlingloff, G. Synlett 1997, 1151-1152. See also Ref. 7.
36. For some recent examples of asymmetric Baeyer-Villiger oxidation, see: Bolm, C.; Schlingloff, G.; Weickhardt, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 1848-1849; Gusso, A.; Baccin, C.; Pinna, F.; Strukul, G. Organometallics 1994, 13, 3442-3451; Bolm, C.; Schlingloff, G. J. Chem. Soc., Chem. Commun. 1995, 1247-1248; Lopp, M.; Paju, A.; Kanger, T.; Pehk, T. Tetrahedron Lett. 1996, 37, 7583-7586; Bolm, C.; Schlingloff, G.; Bienewald, F. J. Mol. Catal. 1997, 117, 347-350; Strukul, G.; Varagnolo, A.; Pinna, F. ibid. 1997, 117, 413-423; Bolm, C.; Luong, T. K. K.; Schlingloff, G. Synlett 1997, 1151-1152. See also Ref. 7.
37. For some recent examples of asymmetric Baeyer-Villiger oxidation, see: Bolm, C.; Schlingloff, G.; Weickhardt, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 1848-1849; Gusso, A.; Baccin, C.; Pinna, F.; Strukul, G. Organometallics 1994, 13, 3442-3451; Bolm, C.; Schlingloff, G. J. Chem. Soc., Chem. Commun. 1995, 1247-1248; Lopp, M.; Paju, A.; Kanger, T.; Pehk, T. Tetrahedron Lett. 1996, 37, 7583-7586; Bolm, C.; Schlingloff, G.; Bienewald, F. J. Mol. Catal. 1997, 117, 347-350; Strukul, G.; Varagnolo, A.; Pinna, F. ibid. 1997, 117, 413-423; Bolm, C.; Luong, T. K. K.; Schlingloff, G. Synlett 1997, 1151-1152. See also Ref. 7.
38. For some recent examples of asymmetric Baeyer-Villiger oxidation, see: Bolm, C.; Schlingloff, G.; Weickhardt, K. Angew. Chem., Int. Ed. Engl. 1994, 33, 1848-1849; Gusso, A.; Baccin, C.; Pinna, F.; Strukul, G. Organometallics 1994, 13, 3442-3451; Bolm, C.; Schlingloff, G. J. Chem. Soc., Chem. Commun. 1995, 1247-1248; Lopp, M.; Paju, A.; Kanger, T.; Pehk, T. Tetrahedron Lett. 1996, 37, 7583-7586; Bolm, C.; Schlingloff, G.; Bienewald, F. J. Mol. Catal. 1997, 117, 347-350; Strukul, G.; Varagnolo, A.; Pinna, F. ibid. 1997, 117, 413-423; Bolm, C.; Luong, T. K. K.; Schlingloff, G. Synlett 1997, 1151-1152. See also Ref. 7.