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AminationO 0268 The Tandem Cope-Type Hydroamination/[2,3]-Rearrangement Sequence:

A Strategy to Favor the Formation of Intermolecular Hydroamination Products and Enable Difficult Cyclizations. — The process allows intermolecular reactions of N-alkyl-N-methallylhydroxylamines to be energetically more favorable: the N-oxide intermediate formed via Cope-type hydroamination can form a more stable neutral product via a [2,3]-Meisenheimer rearrangement. This tandem sequence also leads to increased efficiency in intramolecular systems as is illustrated by synthesis of the alka-loids N-acetyl coniine (XVII) and norreticuline (XXII). — (BOURGEOIS, J.; DION, I.; CEBROWSKI, P. H.; LOISEAU, F.; BEDARD, A.-C.; BEAUCHEMIN*, A. M.; J. Am. Chem. Soc. 131 (2009) 3, 874-875; Dep. Chem., Univ. Ottawa, Ottawa, Ont. K1N 6N5, Can.; Eng.) — Bartels

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ChemInform 2009, 40, issue 22 © 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

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ChemInform 2009, 40, issue 22 © 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim