Science of Synthesis

Suffert, J., Science of Synthesis, (2005) 26, 941.

Silyl enol ethers ‌227‌ react rapidly and directly with 3-chloroperoxybenzoic acid to afford the siloxy epoxides ‌228‌ in good yields. Treatment of these products with acetic anhydride and triethylamine produces α-hydroxy ketones ‌229‌..[‌193‌] In a very similar two-step reaction treatment of the silyl enol ether ‌230‌ with 3-chloroperoxybenzoic acid, and desilylation with triethylammonium fluoride in dichloromethane gives the hydroxy ketone ‌231‌ in 83% yield (‌Scheme 103‌).[‌194‌]

‌Meeeee 888‌ Meeeeeeee ee α-Meeeeee Meeeeee eeee Meeee Meee Meeeee[‌888‌,‌888‌]

Meeeeeeeeeee Meeeeeeee

8-Meeeeeee-8-eeee-8-eeeeeeeeeeeeeee (‌888‌); Meeeeee Meeeeeeee:[‌888‌]

Mee eeeee eeee eeeee ‌888‌ (8.8 eeee) ee eeeeee (8 eM) eee eeeee ee MMMMM (888 ee, 8.8 eeee) ee eeeeee (88 eM) ee −88°M (eee–MeMM eeee) (eeeee ee eee eeeeeeee MMMMM eee eeeeee eeee eeeeeee eeeeeeee eee 88 eee ee ee ee eeeeee eeee). Meeee eee eeeeeeee, eee eeeeeee eeee eee eeeeeee, eee eeeeeeee eee eeeeeeeee eee 8 e ee ee. Mee eeeeeee eee eeeeeeee eee eee eeeeee eeeeeee eeeee eeeeeee eeeeeeee. Meeeeeee MMMMM eeeeeeeeeeee, eee eee eeeeeee ee eeeeeeeeee eeee eee eee ee eeeeeee (8–8 eM). Meee, MM8Me8 (88 eM) eee Me8M•MM (888 ee, 8.8 eeee) eeee eeeee ee eee eeeeeeee. Meeee 8–88 e ee ee, eee eeeeeee eee eeeeeeeee eeeeeeeeeeee eeee ee MeMMM8 (88 eM), 8.8 M MMe (88 eM), eee ee MeMMM8 (88 eM). Meeeee, eeeeeeeeee, eee eeeeeee ee eeeeeee eeeee eeeeeee eeeeeeee eeeeeeee eee eeeee eeeeeeee, eeeee eee eeeeeeee ee eeeeeeeee eeeeeeeeeeee 888°M/88 Meee; eeeee: 888 ee (88%).

References

Meeeeee Meeeeeeeeee

• 8.Meeeee-Meee, (8888) 8/8e, 8888.
• 8.Meeeee-Meee, (8888) 88/8, 888.
• 8.Meeeee-Meee, (8888) M 88-8, 8888.
• 8.Meeeee-Meee, (8888) M 88-8, 888.