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- W2023552602 startingPage "2015" @default.
- W2023552602 abstract "Abstract 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 t BuOK 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, 69451 Weinheim, Germany, 2007)" @default.
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- W2023552602 date "2007-03-27" @default.
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- W2023552602 title "Preparation of α-Acetonylpiperidines from α-Allylated Heterocycles by a Bromocyclocarbamation Reaction" @default.
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- W2023552602 doi "https://doi.org/10.1002/ejoc.200601031" @default.
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