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Enantio- and diastereoselective syntheses of 3-Hydroxypiperidines through iridium-catalyzed allylic substitution

Stereoselective syntheses of 3-hydroxypiperidines have been developed. Key intermediates are N-protected allylamines that are prepared by an enantioselective iridium-catalyzed allylic amination. A subsequent catch and release procedure that involves an epoxidation and base-mediated elimination yield...

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Bibliographic Details
Main Authors: Hoecker, Johannes David (Author) , Rudolf, Georg C. (Author) , Bächle, Florian (Author) , Fleischer, Steffen (Author) , Lindner, Benjamin (Author) , Helmchen, Günter (Author)
Format: Article (Journal)
Language:English
Published: July 2, 2013
In: European journal of organic chemistry
Year: 2013, Issue: 23, Pages: 5149-5159
ISSN:1099-0690
DOI:10.1002/ejoc.201300445
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/10.1002/ejoc.201300445
Verlag, lizenzpflichtig, Volltext: https://chemistry-europe.onlinelibrary.wiley.com/doi/abs/10.1002/ejoc.201300445
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Author Notes:Johannes Hoecker, Georg C. Rudolf, Florian Bächle, Steffen Fleischer, Benjamin D. Lindner, and Günter Helmchen
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Summary:Stereoselective syntheses of 3-hydroxypiperidines have been developed. Key intermediates are N-protected allylamines that are prepared by an enantioselective iridium-catalyzed allylic amination. A subsequent catch and release procedure that involves an epoxidation and base-mediated elimination yields δ-lactams that are suitably functionalized to prepare biologically active 3-hydroxypiperidines. In addition, applications of this method to the total syntheses of deoxymannojirimycin, D-erythro-sphingosine, and chiral building blocks of interest for medicinal chemistry are described.
Item Description:Gesehen am 22.06.2021
Physical Description:Online Resource
ISSN:1099-0690
DOI:10.1002/ejoc.201300445

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