1332531-41-5Relevant articles and documents
Preparation of α-acetonylpiperidines from α-allylated heterocycles by a bromocyclocarbamation reaction
Kuznetsov, Nikolai Yu.,Khrustalev, Victor N.,Godovikov, Ivan A.,Bubnov, Yuri N.
, p. 2015 - 2021 (2007)
2,6-Disubstituted (alkyl)(allyl)- and diallylpiperidines containing C=C bonds in different environments can be selectively transformed into α-acetonylpiperidines, including the alkaloid (±)-6-epipinidinone. The key step is the bromocyclocarbamation reaction of the N-Boc-protected α-allylheterocycle with N-bromosuccinimide. The bulky tert-butyl group on the piperidine ring can affect the diastereoselectivity of the cyclization by 1,5-asymmetric induction. The structure of one of the isolated diastereomers was established by X-ray single-crystal diffraction. The prepared bicyclic bromides were readily dehydrobrominated with tBuOK and the corresponding enols were hydrolyzed to α-acetonylpiperidine hydrochlorides. The method presented is convenient and simple to perform. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.