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37.2.2.3.6 Variation 6: Using Oxone and Oxazolidinone-Containing Chiral Ketones

DOI: 10.1055/sos-SD-037-00167

Goeddel, D.; Shi, Y.Science of Synthesis, (200837312.

Although a wide variety of trans- and trisubstituted epoxides can be prepared in high enantiomeric excess with ketone 19 (Section 37.2.2.3.5), some substrate classes still pose a challenge for dioxirane-mediated epoxidations, including Z- and terminal alkenes. Ketone 21, prepared in six steps from d-glucose, gives good enantiomeric excess for conjugated Z-alkenes and encouragingly high enantiomeric excess values for vinylbenzenes (Table 41).[‌158‌‌160‌]

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