Stereoselective synthesis of 2,4,5-trisubstituted piperidines by carbonylene and Prins cyclisations

Claire Cariou; John Snaith

doi:10.1039/b515547a

Stereoselective synthesis of 2,4,5-trisubstituted piperidines by carbonylene and Prins cyclisations

Claire Cariou, John Snaith

Chemistry

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19 Citations (Scopus)

Abstract

Cyclisation of aldehydes 3a - e catalysed by concentrated hydrochloric acid affords predominantly the all cis 2,4,5trisubstituted piperidines 4a - e when 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.

Original language	English
Pages (from-to)	51-53
Number of pages	3
Journal	Organic and Biomolecular Chemistry
Volume	4
DOIs	https://doi.org/10.1039/b515547a
Publication status	Published - 1 Jan 2006

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title = "Stereoselective synthesis of 2,4,5-trisubstituted piperidines by carbonylene and Prins cyclisations",

abstract = "Cyclisation of aldehydes 3a - e catalysed by concentrated hydrochloric acid affords predominantly the all cis 2,4,5trisubstituted piperidines 4a - e when 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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AB - Cyclisation of aldehydes 3a - e catalysed by concentrated hydrochloric acid affords predominantly the all cis 2,4,5trisubstituted piperidines 4a - e when 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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ER -

Stereoselective synthesis of 2,4,5-trisubstituted piperidines by carbonylene and Prins cyclisations

Abstract

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