Stereoselective synthesis of 2,4,5-trisubstituted piperidines by carbonyl ene and Prins cyclisations |
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| Authors: | Cariou Claire A M Snaith John S |
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| Affiliation: | School of Chemistry, University of Birmingham, Edgbaston, Birmingham, UK B15 2TT. |
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| Abstract: | Cyclisation of aldehydes 3-e catalysed by concentrated hydrochloric acid affords predominantly the all cis 2,4,5-trisubstituted piperidines 4a-ewhen the 2-substituent is small, while catalysis by MeAlCl2 in refluxing chloroform gives the trans piperidines 5a-e with diastereomeric ratios of up to 99:1. |
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