one-pot two-step organocatalytic asymmetric synthesis of spirocyclic piperidones via wolff rearrangement–amidation–michael–hemiaminalization sequence
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2017
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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%.
| Reference Key |
liu2017catalystsone-pot
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|---|---|
| Authors | ;Yanqing Liu;Liang Ouyang;Ying Tan;Xue Tang;Jingwen Kang;Chunting Wang;Yaning Zhu;Cheng Peng;Wei Huang |
| Journal | journal of essential oil research |
| Year | 2017 |
| DOI |
10.3390/catal7020046
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| URL | |
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