Addition-type oxidation of silylalkene using ozone: An efficient approach for acyloin and its derivatives

Chemistry Letters

Volumn 40, Issue 3, 2011, Pages 233-235

  Igawa, Kazunobu ^a   Kawasaki, Yuuya ^a   Tomooka, Katsuhiko ^a  

^a KYUSHU UNIVERSITY   (Japan)

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[No Author keywords available]

Indexed keywords

EID: 79951906222     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2011.233     Document Type: Article

References (42)

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17. Büchi and Wüest have reported the oxidation of trimethylsilyl alkenes affording acyloins with reductive workup in the '70s, in which they proposed trimethylsilyl peroxide and dioxetane as intermediates, see: a) G. Büchi, H. Wüest, J. Am. Chem. Soc. 1978, 100, 294. Although their trimethylsilyl-substituted intermediate is too reactive to be handled with ease, our silyl peroxides having bulky silyl group are isolable and hence a variety of transformation is available. Renaud and colleagues have also reported ozone oxidation of 2-trimethylsilyl-substituted terminal alkenes which afforded the corresponding hydroxymethyl ketones, see
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19. Anderson and colleagues have reported a preparation of α-hydroxy ketone by ozone oxidation of silyl-substituted internal alkene followed by hydrolysis. However, we speculate that there is a possibility that their product is some sort of α-peroxy ketone not α-hydroxy ketone, based on their experimental data: J. C. Anderson, J. G. Ford, M. Whiting, Org. Biomol. Chem. 2005, 3, 3734.
20. Avery and colleagues utilized ozone oxidation of 1-trimethylsilyl- substituted terminal alkenes to construct the A/B ring of artemisinin: a) M. A. Avery, C. Jennings-White, W. K. M. Chong, J. Org. Chem. 1989, 54, 1789.
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28. Few examples of ruthenium-catalyzed oxidation of alkene to acyloin were reported: a) S. Murahashi, T. Saito, H. Hanaoka, Y. Murakami, T. Naota, H. Kumobayashi, S. Akutagawa, J. Org. Chem. 1993, 58, 2929.
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35. 2, or hexane as the solvent.
36. We performed single-crystal X-ray diffraction analysis of silylperoxy ketone 3a. Crystallographic data of 3a has been deposited with Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-804366. Copies of the data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk/conts/retrieving. html.
37. Ph3SiOH was obtained in 58% yield with complex mixture by the ozone oxidation of (Z)-2a followed by reductive work up with Me2S.
38. D. Brandes, A. Blaschette, J. Organomet. Chem. 1975, 99, C33.
39. Recently, Woerpel and colleagues investigated in detail the mechanism of phosphine reduction of silyl peroxide: J. R. Harris, M. T. Haynes, II, A. M. Thomas, K. A. Woerpel, J. Org. Chem. 2010, 75, 5083.
40. Phosphite reductions following ozone oxidation of 2e2h were performed without purification of 3e3h to avoid their slight decomposition by silica gel column chromatography.
41. Ozone oxidations of 2f2h were performed without separation of the E/Z isomers; see Supporting Information.21 20 Although, ozone is capable of oxidizing benzylic carbon, no such products were observed in the ozone oxidation of 2f2h.
42. Supporting Information is available electronically on the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/index.html.