Asymmetric Baeyer-Villiger reaction: Diastereodifferentiating peracid oxidation of chiral acetal in the presence of Lewis acid

Tetrahedron Letters

Volumn 38, Issue 34, 1997, Pages 6019-6022

  Sugimura, Takashi ^a   Fujiwara, Yoshihisa ^a   Akira, Tai ^a  

^a UNIVERSITY OF HYOGO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

GAMMA LACTONE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; OXIDATION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030873410     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01338-5     Document Type: Article

References (34)

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13. Several kinetic resolutions of racemic mixtures of chiral ketones by chemical means have been reported. One of them (ref. d) included an example of enantiotopos differentiation of prochiral ketone. (a) Bolm, C.; Schlingloff, G.; Weickhardt, K. Angew. Chem. Int. Ed. Eng. 1994, 33, 1848-1849.
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17. For a recent comprehensive review of Baeyer-Villiger oxidation, see: Krow, G. R. in Organic Chemistry, Vol. 43, 1993, John Wiley: pp. 251-798.
18. Criegee, R. Justus Liebigs Ann. Chem. 1948, 560, 127-135.
19. Reaction of acyclic acetal (such as diethyl acetal) with MCPBA affords the carbonate orthoester as the result of dual Baeyer-Villiger reaction, whereas that of cyclic acetal does not proceed. (a) Bailey, W. F.; Sikh, M. J. Am. Chem. Soc. 1982, 104, 1769-1771.
20. (b) Bailey, W. F.; Bischoff, J. J., J. Org. Chem. 1985, 50, 3009-3016.
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22. When the reaction was worked-up under basic conditions, a diastereomeric mixture of 3 with a small amount of 4 was obtained.
23. 3. Short silica gel column afforded chemically pure 4 in 95-98% yield. The enantiomeric excess of 4 was determined by chiral capillary GLC (CP-Chirasil-β-DEX CB) or chiral HPLC analyses (CHIRALCEL OD or CHIRALPAK AD) under baseline separation.
24. Absolute structure of 4a. For phenyl analog, Helmchen, G.; Nul, G. Angew. Chem. Int. Ed. Engl. 1979, 18, 65-66. For 4-methylphenyl, Lawston, I. W.; Inch, T. D. J. Chem. Soc., Perkin Trans. I 1983, 2629-2635. For 4-chlorophenyl, Lawston, I. W.; Inch, T. D. J. Chem. Soc., Perkin Trans. I 1983, 2629-2635. For butyl, Kosugi, H.; Tagami, K.; TAkahashi, A.; Kanna, H.; Uda, H. J. Chem. Soc., Perkin Trans. I 1989, 935-943. For isopropyl, King, Chi-Hsin. R.; Poulter, C. D. J. Am. Chem. Soc. 1982, 104, 1413-1420.
25. Absolute structure of 4a. For phenyl analog, Helmchen, G.; Nul, G. Angew. Chem. Int. Ed. Engl. 1979, 18, 65-66. For 4-methylphenyl, Lawston, I. W.; Inch, T. D. J. Chem. Soc., Perkin Trans. I 1983, 2629-2635. For 4-chlorophenyl, Lawston, I. W.; Inch, T. D. J. Chem. Soc., Perkin Trans. I 1983, 2629-2635. For butyl, Kosugi, H.; Tagami, K.; TAkahashi, A.; Kanna, H.; Uda, H. J. Chem. Soc., Perkin Trans. I 1989, 935-943. For isopropyl, King, Chi-Hsin. R.; Poulter, C. D. J. Am. Chem. Soc. 1982, 104, 1413-1420.
26. Absolute structure of 4a. For phenyl analog, Helmchen, G.; Nul, G. Angew. Chem. Int. Ed. Engl. 1979, 18, 65-66. For 4-methylphenyl, Lawston, I. W.; Inch, T. D. J. Chem. Soc., Perkin Trans. I 1983, 2629-2635. For 4-chlorophenyl, Lawston, I. W.; Inch, T. D. J. Chem. Soc., Perkin Trans. I 1983, 2629-2635. For butyl, Kosugi, H.; Tagami, K.; TAkahashi, A.; Kanna, H.; Uda, H. J. Chem. Soc., Perkin Trans. I 1989, 935-943. For isopropyl, King, Chi-Hsin. R.; Poulter, C. D. J. Am. Chem. Soc. 1982, 104, 1413-1420.
27. Absolute structure of 4a. For phenyl analog, Helmchen, G.; Nul, G. Angew. Chem. Int. Ed. Engl. 1979, 18, 65-66. For 4-methylphenyl, Lawston, I. W.; Inch, T. D. J. Chem. Soc., Perkin Trans. I 1983, 2629-2635. For 4-chlorophenyl, Lawston, I. W.; Inch, T. D. J. Chem. Soc., Perkin Trans. I 1983, 2629-2635. For butyl, Kosugi, H.; Tagami, K.; TAkahashi, A.; Kanna, H.; Uda, H. J. Chem. Soc., Perkin Trans. I 1989, 935-943. For isopropyl, King, Chi-Hsin. R.; Poulter, C. D. J. Am. Chem. Soc. 1982, 104, 1413-1420.
28. Absolute structure of 4a. For phenyl analog, Helmchen, G.; Nul, G. Angew. Chem. Int. Ed. Engl. 1979, 18, 65-66. For 4-methylphenyl, Lawston, I. W.; Inch, T. D. J. Chem. Soc., Perkin Trans. I 1983, 2629-2635. For 4-chlorophenyl, Lawston, I. W.; Inch, T. D. J. Chem. Soc., Perkin Trans. I 1983, 2629-2635. For butyl, Kosugi, H.; Tagami, K.; TAkahashi, A.; Kanna, H.; Uda, H. J. Chem. Soc., Perkin Trans. I 1989, 935-943. For isopropyl, King, Chi-Hsin. R.; Poulter, C. D. J. Am. Chem. Soc. 1982, 104, 1413-1420.
29. For isobutyl, Gagnon, R.; Grogan, G.; Groussain, E.; Pedragosa-Moreau, S.; Richardson, P. F.; Roberts, S. M.; Willetts, A. J.; Alphand, V.; Lebreton, J.; Furstoss, R. J. Chem. Soc., Perkin Trans. I 1995, 2527-2528.
30. Because MCPBA employed included 18% m-chlorobenzoic acid, the total amount of carbonyl compounds through the reaction is 1.22 times that of the indicated MCPBA equivalent.
31. Yamamoto, Y.; Nishii, S.; Yamada, J. J. Am. Chem. Soc. 1986, 108, 7116-7117.
32. Sugimura, T.; Tai, A.; Koguro, K. Tetrahedron 1994, 50, 11647-11658 and references therein.
33. Both enantiomers of DMHD were available from Wako Chemicals, Inc. The preparation method by asymmetric catalytic hydrogenation was also reported. Tai, A.; Kikukawa, T.; Sugimura, T.; Inoue, Y.; Abe, S.; Osawa, T.; Harada, T. Bull. Chem. Soc. Jpn. 1994, 67, 2473-77.
34. 4 resulted in the addition ratio of anti/syn = 87/13, which was lower than that from phenyl substituted 2.