A Two-Step, Formal [4 + 2] Approach toward Piperidin-4-ones via Au Catalysis
Journal of the American Chemical Society2009Vol. 131(24), pp. 8394–8395
Citations Over TimeTop 1% of 2009 papers
Abstract
An efficient, formal [4 + 2] synthesis of synthetically valuable piperidin-4-ones from secondary amines in two steps has been achieved via a key gold catalysis without the purification of tertiary amine intermediates. This reaction is selective toward the less-substituted alkyl group and shows moderate to excellent diastereoselectivities. Its synthetic potential in alkaloid synthesis is demonstrated in a highly diastereoselective synthesis of (+/-)-cermizine C.
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