Discussion Addendum for: Preparation of α‐Acetoxy Ethers by the Reductive Acetylation of Esters:
            <i>endo</i>
            ‐1‐Bornyloxyethyl Acetate

Sizemore, Nicholas; Rychnovsky, S. D.

doi:10.1002/0471264229.os089.16

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“…With suitable substitution at the oxonium ion, the substrate could be engaged in Prins cyclization,19 as well as in Sakurai–Ritter–Prins,20 Cope–Prins,21 and oxa‐Pictet–Spingler rearrangements 22. The preparation of mixed O ‐acyl acetals, as well as numerous applications of oxocarbenium ions generated from these mixed acetals, were recently reviewed by Rychnovsky 12b,23…”

Section: Reactivity Towards Electrophilesmentioning

confidence: 99%

Aluminum Acetals in Organic Synthesis

et al. 2013

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Aluminum acetals are easily obtained from esters and lactones by reduction with aluminum hydrides. These thermally unstable tetrahedral intermediates have found applications in organic synthesis, with various methodologies taking advantage both of the stabilities of these aluminum species at low temperatures and of their tendencies to undergo rearrangement into the corresponding aldehydes. Efficient one‐pot transformations can be achieved from aluminum acetals under ionic and radical conditions. A comprehensive overview of the reactivity of these species, including the most recent advances in this field, is presented in this microreview.

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Section: Reactivity Towards Electrophilesmentioning

confidence: 99%