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Enantioselective Organocatalytic Iodination-Initiated Wagner–Meerwein Rearrangement

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Published in Organic Letters. 2013, vol. 15, no. 22, p. 5890-5893
Abstract The present manuscript describes a high-yielding enantioselective semipinacol transposition, initiated by an electrophilic iodination event. The title transformation makes use of the anionic phase-transfer catalysis (PTC) paradigm for chirality induction. Thus, when combined appropriately, the insoluble cationic iodinating reagent S9 and the lipophilic phosphoric acid L9 act as an efficient source of chiral iodine that performs the semipinacol transposition of strained allylic alcohols Ax to β-iodo spiroketones Bx in good yields and with high levels of diastereo- and enantio-induction. The product β-iodo spiroketones could be derivatized stereospecifically and without stereoerosion, giving rise to products inaccessible directly from a semipinacol rearrangement.
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Other version: http://pubs.acs.org/doi/abs/10.1021/ol402981z
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ROMANOV MICHAILIDIS, Fedor, GUENEE, Laure, ALEXAKIS, Alexandre. Enantioselective Organocatalytic Iodination-Initiated Wagner–Meerwein Rearrangement. In: Organic Letters, 2013, vol. 15, n° 22, p. 5890-5893. https://archive-ouverte.unige.ch/unige:31110

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Deposited on : 2013-11-18

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