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29.7.2.1.1.3 Variation 3: Reactions of Enol Ethers with 1,2-Diols

DOI: 10.1055/sos-SD-029-00442

Cordier, C.; Leach, S.; Nelson, A.Science of Synthesis, (200729437.

The synthesis of 1,3-dioxolanes by reaction of enol ethers with 1,2-diols provides an efficient and mild approach for the protection of 1,2-diols. The catalysts that are usually used to facilitate the reaction are generally similar to those used for the transacetalization of acetals (Section 29.7.2.1.1.2). Since the reagent used is an enol ether, the variation is limited to the synthesis of acetals that would otherwise be derived from enolizable aldehydes or ketones. The most common enol ethers used in the variation are 2-methoxypropene (isopropenyl methyl ether, 156), its ethoxy analogue 157, and 1-methoxycyclohex-1-ene (158) (Scheme 45).

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Meeeeeeeeeee Meeeeeeee

(8M,8eM,8eM,8M,8eM,8M)-8,8,8-Meeeeeeee-8-eeee-8-eeee-8e,8,8e,8,8e,8e-eeeeeeeee-8,8,8,8-eeeeeeee-ee-eeeeeee-8-eee (888); Meeeeee Meeeeeeee:[‌888‌]

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(8M,8M)-8-[Mee(8-eeeeeeeeeeeee)eeeeee]-8,8,8-eeeeeeeee-8,8-eeeeeeeee (888); Meeeeee Meeeeeeee:[‌888‌]

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(±)-8,8-M-Meeeeeeeeeeeeee-eee-eeeeeeee (888):[‌888‌]

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8,8-M-Meeeeeeeeeeeee-M-eeeeee (888):[‌888‌]

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(8eM*,8eM*)-8,8,8e-Meeeeeeeeeeeeeeeeee-8,8-eeeeeeeeeee-8(8eM)-eee (888); Meeeeee Meeeeeeee:[‌888‌]

8-Meeeeeeeeeeeee (8.88e, 88.8eeee) eee eeeee ee e eeeeeee eeee ee eee eeee 888 (8.88e, 88.8eeee) eee MMMM (888ee, 8.888eeee) ee MM8Me8 ee 8°M. Mee eeeeeee eee eeeeeee ee eeee ee ee, eeeeeee eee 88e, eeeeeee eeee MM8Me8 (88eM), eee eeeeee eeee eee. ee MeMMM8 eeee (88eM) eee eeeee (88eM). Mee eeeeeee eeeee eee eeeee (MeMM8) eee eeeeeeeeeeee eeeee eeeeeee eeeeeeee. Meeeeeeeeeee eee ee eeeee eeeeeeeeeeeeee; eeeee: 8.88e (88%).

References


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