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37.2.2.3.5 Variation 5: Using Oxone or Hydrogen Peroxide and Fructose-Derived Chiral Ketones

DOI: 10.1055/sos-SD-037-00167

Goeddel, D.; Shi, Y.Science of Synthesis, (200837308.

Although numerous ketones have been prepared for asymmetric epoxidation, catalysts derived from sugars have demonstrated a broad substrate scope.[‌146‌‌175‌] Fructose-derived ketone 19 gives high enantiomeric excess values for a wide variety of E- and trisubstituted alkenes (Table 35).[‌146‌‌149‌] 2,2-Disubstituted vinylsilanes are also effective substrates, and when treated with tetrabutylammonium fluoride, yield 2,2-disubstituted oxiranylsilanes.[‌150‌]

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Meeee Meeeeee ee (%) Meeee (%) Mee
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Meeee Meeee Meeeeee Meeee Meeeeee Meeee ee (%) Meeee (%) Mee
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Meeee Meeeeee ee (%) Meeee (%) Mee
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(8M,8M)-8-Meeeee-8-eeeeeeeeeeeee (Meeee 88, Meeee 8); Meeeeee Meeeeeeee:[‌888‌]

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References


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