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Title: Approaches to syn-7-substituted 2-azanorbornanes as potential nicotinic agonists; Synthesis of syn- and anti-isoepibatidine
Authors: Malpass, J. R.
Handa, S.
White, R.
First Published: 2005
Citation: Organic Letters, 2005, 7 (13), pp.2759-2762
Abstract: Coupling of N-Boc-7-bromo-2-azabicyclo[2.2.1]heptane with aryl and pyridyl boronic acids incorporates aryl and heterocyclic substituents at the 7-position and leads to a preference for syn over anti stereoisomers. Incorporation of a chloropyridyl group followed by N-deprotection gives syn-isoepibatidine. Facial selectivity in attack on 7-keto-2-azanorbornanes depends heavily on the N-protecting group leading to the first syn-7-hydroxy-2-azabicyclo[2.2.1]heptane derivative.
DOI Link: 10.1021/ol0510365
ISSN: 1523-7060
Type: Article
Appears in Collections:Published Articles, Dept. of Chemistry

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