Hydroxyselanylation of acyloxycyclohex-3-enes
Sweeney, J. B., Haughan, A. F., Knight, J. R. and Thobhani, S. (2007) Hydroxyselanylation of acyloxycyclohex-3-enes. Tetrahedron, 63 (12). pp. 2729-2737. ISSN 0040-4020
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To link to this article DOI: 10.1016/j.tet.2006.12.035
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. (c) 2007 Published by Elsevier Ltd.