Ahmad, S., Thomas, L.H. and Sutherland, A. (2011) Stereoselective synthesis of polyhydroxylated aminocyclohexanes. Organic and Biomolecular Chemistry, 9, pp. 2801-2808. (doi: 10.1039/C0OB00619J)
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Publisher's URL: http://dx.doi.org/10.1039/C0OB00619J
Abstract
The stereoselective synthesis of a series of di- and tri-hydroxylated aminocyclohexane derivatives has been developed. A one-pot, two step tandem process involving an Overman rearrangement and a ring closing metathesis reaction has been utilised for the asymmetric synthesis of (1S)-1-(2′,2′,2′-trichloromethylcarbonylamino)cyclohexa-2-ene. Oxidation of this cyclohexene derivative was then studied leading to the preparation of two diol analogues in excellent stereoselectivity. (1S)-1-(2′,2′,2′-trichloromethylcarbonylamino)cyclohexa-2-ene was then converted to a novel allylic alcohol via a 4,5-dihydro-1,3-oxazole. Functionalisation of this allylic alcohol by Upjohn dihydroxylation conditions or by a directed epoxidation/hydrolysis sequence of reactions allowed the synthesis of two dihydroconduramines in excellent stereoselectivity. The stereochemical assignment of all compounds prepared was confirmed by NOE experiments or X-ray structure determination.
Item Type: | Articles |
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Status: | Published |
Refereed: | Yes |
Glasgow Author(s) Enlighten ID: | Thomas, Dr Lynne and Sutherland, Professor Andrew |
Authors: | Ahmad, S., Thomas, L.H., and Sutherland, A. |
Subjects: | Q Science > QD Chemistry |
College/School: | College of Science and Engineering > School of Chemistry |
Journal Name: | Organic and Biomolecular Chemistry |
Journal Abbr.: | Org. Biomol. Chem. |
ISSN: | 1477-0520 |
ISSN (Online): | 1477-0539 |
Published Online: | 02 March 2011 |
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