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Economical Access to Diverse Enantiopure Tetrahydropyridines and Piperidines Enabled by Catalytic Borrowing Hydrogen.
- Source :
-
Angewandte Chemie International Edition . 1/9/2023, Vol. 62 Issue 2, p1-9. 9p. - Publication Year :
- 2023
-
Abstract
- We disclose herein a catalytic borrowing hydrogen method that enables an unprecedented, economical one‐pot access to enantiopure tetrahydropyridines with minimal reagent use or waste formation. This method couples a few classes of readily available substrates with commercially available 1,3‐amino alcohols, and delivers the valuable tetrahydropyridines of different substitution patterns free of N‐protection. Such transformations are highly challenging to achieve, as multiple redox steps need to be realized in a cascade and numerous side reactions including a facile aromatization have to be overcome. Highly diastereoselective functionalizations of tetrahydropyridines also result in a general access to enantiopure di‐ and tri‐substituted piperidines, which ranks the topmost frequent N‐heterocycle in commercial drugs. [ABSTRACT FROM AUTHOR]
- Subjects :
- *HYDROGEN
*AROMATIZATION
*OXIDATION-reduction reaction
*ALCOHOL
*PIPERIDINE
Subjects
Details
- Language :
- English
- ISSN :
- 14337851
- Volume :
- 62
- Issue :
- 2
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie International Edition
- Publication Type :
- Academic Journal
- Accession number :
- 161103365
- Full Text :
- https://doi.org/10.1002/anie.202212528