Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2007, Issue 12, Pages 2015-2021Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200601031
Keywords
alkaloids; allylic compounds; boranes; nitrogen heterocycles; halocyclocarbamation
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2,6-Disubstituted (alkyl)(allyl)- and diallylpiperidines containing C=C bonds in different environments can be selectively transformed into alpha-acetonylpiperidines, including the alkaloid (+/-)-6-epipinidinone. The key step is the bromocyclocarbamation reaction of the N-Boc-protected alpha-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 struclure 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 alpha-acetonylpiperidine hydrochlorides. The method presented is convenient and simple to perform. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007).
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