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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Veröffentlicht in:European journal of organic chemistry Jg. 2013; H. 23; S. 5149 - 5159
Hauptverfasser: Hoecker, Johannes, Rudolf, Georg C., Bächle, Florian, Fleischer, Steffen, Lindner, Benjamin D., Helmchen, Günter
Format: Journal Article
Sprache:Englisch
Veröffentlicht: Weinheim WILEY-VCH Verlag 01.08.2013
WILEY‐VCH Verlag
Wiley
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Schlagworte:
Alkaloids
Amination
Azasugars
Chemistry
Chemistry, Organic
Epoxidation
Iridium
Lact­ams
Nitrogen heterocycles
Pharmaceutical industry
Physical Sciences
Science & Technology
Lactams
DEOXYMANNOJIRIMYCIN
Azasugars
Alkaloids
CARBONYLATION
Nitrogen heterocycles
Amination
PIPERIDINE
Epoxidation
ENANTIOSELECTIVE SYNTHESES
Iridium
STEREOSELECTIVE-SYNTHESIS
ASYMMETRIC TOTAL-SYNTHESIS
DERIVATIVES
EFFICIENT
CYCLIZATION
ISSN:1434-193X, 1099-0690
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Zusammenfassung: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. Stereoselective syntheses of 3‐hydroxypiperidines are reported. The key reactions are an iridium‐catalyzed allylic amination and a catch and release procedure that consists of a highly diastereoselective epoxidation and a base‐mediated ring opening of the epoxide. This method was applied to the total syntheses of sphingosine, deoxymannojirimycin, and pharmaceutically relevant small molecules.
Bibliographie:istex:AE9F99A7F63E711620A8E0156378809EBCE247B1
ark:/67375/WNG-F0R9Q4T2-F
ArticleID:EJOC201300445
These authors contributed equally.
ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
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ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201300445