Science of Synthesis

Smith, L. H. S.; Coote, S. C.; Procter, D. J., Science of Synthesis Knowledge Updates, (2010) 3, 481.

Acyclic 1,1-diacyloxy compounds derived from ketones tend to be unstable under the acidic reaction conditions used to form acylals from aldehydes, and few examples of the formation of acyclic gem-diacylates in good yield from ketones and acid anhydrides have been published.[‌15‌,‌28‌] However, cyclic 1,1-diacyloxy derivatives of ketones are formed much more readily. Under acidic conditions, oxo dicarboxylic acids can cyclize to give fused bicyclic[‌29‌] or spirocyclic acylals,[‌30‌] such as ‌4‌ or ‌5‌, respectively (‌Scheme 7‌).

‌Meeeee 8‌ Meeeeeeeeee ee Mee Meeeeee Me Meee 8,8-Meeeeeeeee[‌88‌,‌88‌]

Mee eeeee eeeeeee eeeeeeeeeee ee eee eeeeeeee ee e eeeeeeeeee eeee eeeeeeeee ee eeee eeeeeeeeee eee-eeeeeeeee eeeeeeeee, eeee ee ‌8‌ (‌Meeeee 8‌).

‌Meeeee 8‌ Meeeeeeeeee ee Mee Meeee Me Meee Meeeeeeeee 8,8-Meeeeeeeee[‌88‌,‌88‌]

Meeeeeeeeeee Meeeeeeee

88,88-Me[(M)-eeeeeeeeeee]-88,88-eeeeeeeeeeeeeee[8.8.8.88,8.88,8]eeeeeeeee-8,8,8-eeeeee-88,88-eeeee (‌8‌); Meeeeee Meeeeeeee:[‌88‌]

Me e eeee ee 8,8-eee[(8M)-8-eeeeeee-8-eeeeeeeeee-8-eeee]eeeee-8-eee (8.888 e, 8.8 eeee) ee eee MM8Me8 (8 eM) eee eeeee MMMM (8.88 e, 8 eeee). Meeee eeeee eeeeeee eee 8.8 e ee ee eeeee M8, eee eeeeeee eee eeeeeee eeee M8M (88 eM) eee eeeeeeeee eeee MM8Me8 (8 × 88 eM). Mee eeeeeeee eeeeeee eeeee eee eeeee (Me8MM8). Meeeeeeeeeeeeee (MeMMe/eeeeeee 8:8) eeee e eeeeeeeeeee eeeee; eeeee: 8.88 e (88%).

8-(8-Meeeeee-8-eee-8,8-eeeeeeeeeeee[e]eeeee-8-ee)-8-eeeeeeeeeeee Meeeeee (‌8‌); Meeeeee Meeeeeeee:[‌88‌]

8-(8-Meeeee-8-eeeeeeeeeeeeee)eeeeeee eeee (8.88 e, 8.88 eeee) eee eeeeeeeee ee Me8M (88 eM) eee MeMMe (8.8 e, 88.8 eeee, 88.8 eeeee) eee eeeee. Mee eeee eee eeeeee eeeee eeeeee eee 8 e eee eeee eeeeee eeee eeeeeee eee, eee eee eeeeeeeeeee eee eeeeeeeee ee eeeeeeeeee, eeeeee eeee M8M, eee eeeee; eeeee: 8.88 e (88%).

References