Accessibility navigation


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

Full text not archived in this repository.

It is advisable to refer to the publisher's version if you intend to cite from this work. See Guidance on citing.

To link to this item DOI: 10.1016/j.tet.2006.12.035

Abstract/Summary

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.

Item Type:Article
Refereed:Yes
Divisions:Faculty of Life Sciences > School of Chemistry, Food and Pharmacy > Department of Chemistry
ID Code:11647
Uncontrolled Keywords:CURTIN-HAMMETT PRINCIPLE, CONDURITOL B-DERIVATIVES, REGIOSELECTIVE-SYNTHESIS, DIASTEREOSELECTIVE SYNTHESIS, ALLYLIC ALCOHOLS, ACETOXYCYCLOHEX-2-ENE, HYDROXYSELENATION, CHEMISTRY, ADDITIONS, INOSITOL

University Staff: Request a correction | Centaur Editors: Update this record

Page navigation