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Hydroxyselanylation of acyloxycyclohex-3-enes

Sweeney, Joseph B., Haughan, Alan F., Knight, J.R. and Thobhani, Smita (2007) Hydroxyselanylation of acyloxycyclohex-3-enes. Tetrahedron, 63 (12). pp. 2729-2737. ISSN 0040-4020

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In contrast to the corresponding hydroxyiodination reactions, the reaction of acetoxycyclohex-2-ene 1 with N-PSP in the presence of water shows little regiocontrol, but is highly diastereoselective. However, the same reaction of the (R)-phenylglycinate derivative of (±)-cyclohexen-3-ol is highly diastereoselective, and regioselective. A hydrogen-bonding interaction is proposed to rationalize these differing selectivities.

Item Type: Article
Subjects: Q Science > QD Chemistry
Schools: School of Applied Sciences
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Depositing User: Joseph Sweeney
Date Deposited: 09 Oct 2012 08:55
Last Modified: 28 Aug 2021 11:22


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