Stereoselective synthesis of alicyclic ketones: A hydrogen borrowing approach |
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Authors: | Roly J. Armstrong Wasim M. Akhtar James R. Frost Kirsten E. Christensen Neil G. Stevenson Timothy J. Donohoe |
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Affiliation: | 1. Chemistry Research Laboratory, University of Oxford, Oxford, OX1 3TA, United Kingdom;2. GlaxoSmithKline, Medicines Research Centre, Stevenage, SG1 2NY, United Kingdom |
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Abstract: | A highly diastereoselective annulation strategy for the synthesis of alicyclic ketones from diols and pentamethylacetophenone is described. This process is mediated by a commercially available iridium(III) catalyst, and provides efficient access to a wide range of cyclopentane and cyclohexane products with high levels of stereoselectivity. The origins of diastereoselectivity in the annulation reaction have been explored by a series of control experiments, which provides an explanation for how each stereocentre around the newly forged ring is controlled. |
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Keywords: | Corresponding author. Hydrogen borrowing catalysis Iridium Diastereoselective Cyclopentanes Cyclohexanes |
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