Stereoselective synthesis of polyhydroxylated aminocyclohexanes

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)

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
• 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