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Asymmetric synthesis of erythro- and threo-2-(1-hydroxyalkyl)piperidines via iodocyclocarbamation of 1-acyl-2-alkenyl-1,2,3,6-tetrahydropyridines

✍ Scribed by Daniel L Comins; Alfred L Williams

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
121 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

An iodocyclocarbamation procedure has been developed for the stereoselective preparation of erythro-and threo-2-(1-hydroxyalkyl)piperidines. This methodology was utilized in the asymmetric synthesis of two piperidine alkaloids, (+)-Ξ±-conhydrine and (+)-Ξ²-conhydrine.

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## Abstract New procedures are described for the synthesis of Ξ±,β‐ethylenic and acetylenic aldehydes from 2‐butene‐ and 2‐butyne‐1,4‐diol, respectively (see __Scheme 1__). These are applied to the preparation of a particular δ‐acetylamino‐α,β‐ethylenic aldehyde ((__E__)‐**5**) as well as of its ace