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Issue 8, 2011
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Stereoselective synthesis of polyhydroxylated aminocyclohexanes

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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 alcoholvia 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.

Graphical abstract: Stereoselective synthesis of polyhydroxylated aminocyclohexanes

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Supplementary files

Article information


Submitted
23 Aug 2010
Accepted
31 Jan 2011
First published
02 Mar 2011

Org. Biomol. Chem., 2011,9, 2801-2808
Article type
Paper

Stereoselective synthesis of polyhydroxylated aminocyclohexanes

S. Ahmad, L. H. Thomas and A. Sutherland, Org. Biomol. Chem., 2011, 9, 2801
DOI: 10.1039/C0OB00619J

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