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Stereoselective synthesis of 2-dienyl-substituted piperidines using an eta(4)-dienetricarbonyliron complex as the stereocontrolling element in a double reductive amination cascade

Williams, I., Reeves, K., Kariuki, Benson and Cox, Liam R. 2007. Stereoselective synthesis of 2-dienyl-substituted piperidines using an eta(4)-dienetricarbonyliron complex as the stereocontrolling element in a double reductive amination cascade. Organic & Biomeolecular Chemistry 5 (20) , pp. 3325-3329. 10.1039/b710898b

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Abstract

In the presence of NaBH(OAc)(3), a 1,5-keto-aldehyde, contained within a side-chain of an eta(4)-dienetricarbonyliron complex, undergoes a double reductive amination sequence with a series of primary amines, to provide the corresponding piperidine products in good to excellent yield. The dienetricarbonyliron complex functions as a powerful chiral auxiliary in this cascade process, exerting complete control over the stereoselectivity of the reaction, with the formation of a single diastereoisomeric product. The sense of stereoinduction has been confirmed by X-ray crystallography. Removal of the tricarbonyliron moiety can be effected with CuCl2 to afford the corresponding 2-dienyl-substituted piperidine in excellent yield. Attempted extension of this cyclisation strategy to the corresponding azepane ring system using a 1,6-keto-aldehyde as the cyclisation precursor was unsuccessful; in this case, the reaction stopped after a single reductive amination on the aldehyde to provide an acyclic keto-amine product.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Publisher: RCS Publishing
ISSN: 1477-0520
Last Modified: 04 Jun 2017 04:59
URI: http://orca-mwe.cf.ac.uk/id/eprint/47175

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