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29.18.1.1.2.2 Variation 2: Using an Oxo Acid

DOI: 10.1055/sos-SD-129-00201

Smith, L. H. S.; Coote, S. C.; Procter, D. J.Science of Synthesis Knowledge Updates, (20103481.

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).

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

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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]

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