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J Am Chem Soc. 2009 Jun 24;131(24):8394-5. doi: 10.1021/ja903531g.

A two-step, formal [4 + 2] approach toward piperidin-4-ones via Au catalysis.

Author information

1
Department of Chemistry/216, University of Nevada, Reno, 1664 North Virginia Street, Reno, Nevada 89557, USA.

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.

PMID:
19492799
DOI:
10.1021/ja903531g
[Indexed for MEDLINE]

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