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1.5.2.3.1.2.2 Termination with a Rearrangement

DOI: 10.1055/sos-SD-219-00174

Wang, S.-H.; Tu, Y.-Q.; Tang, M.Science of Synthesis: Applications of Domino Transformations in Organic Synthesis, (20151316.

As mentioned in Section 1.5.2.1.4 on Prins–pinacol rearrangements, the Prins cyclization can also be followed in situ by a pinacol-type (or semipinacol-type) rearrangement to give a cyclic product. This type of domino transformation was first reported by Mousset and co-workers and further developed by the Overman group.[‌84‌,‌85‌] Now it is broadly named as the Prins–pinacol rearrangement. Similar to Prins–polyene cyclizations, it can be initiated intermolecularly or intramolecularly. For the intramolecular cases, a ring-closure process is generally involved, while the intermolecular processes remain underexplored and often suffer from mediocre stereoselectivity.

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