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- Title
One-Pot Two-Step Organocatalytic Asymmetric Synthesis of Spirocyclic Piperidones via Wolff Rearrangement--Amidation--Michael--Hemiaminalization Sequence.
- Authors
Yanqing Liu; Liang Ouyang; Ying Tan; Xue Tang; Jingwen Kang; Chunting Wang; Yaning Zhu; Cheng Peng; Wei Huang
- Abstract
A highly enantioselective organocatalytic Wolff rearrangement-amidation-Michael-hemiaminalization stepwise reaction is described involving a cyclic 2-diazo-1,3-diketone, primary amine and α ,β-unsaturated aldehyde. Product stereocontrol can be achieved by adjusting the sequence of steps in this one-pot multicomponent reaction. This approach was used to synthesize various optically active spirocyclic piperidones with three stereogenic centers and multiple functional groups in good yields up to 76%, moderate diastereoselectivities of up to 80:20 and high enantioselectivities up to 97%.
- Subjects
ASYMMETRIC synthesis; PIPERIDONES; ORGANOCATALYSIS
- Publication
Catalysts (2073-4344), 2017, Vol 7, Issue 2, p46
- ISSN
2073-4344
- Publication type
Article
- DOI
10.3390/catal7020046