One-Pot Two-Step Organocatalytic Asymmetric Synthesis of Spirocyclic Piperidones via Wolff Rearrangement–Amidation–Michael–Hemiaminalization Sequence

Catalysts

Yaning Zhu¹  Ying Tan¹  Cheng Peng²  Wei Huang²  Xue Tang²  Jingwen Kang²  Yanqing Liu²  Chunting Wang³  Liang Ouyang³ 

[1] China Resources Sanjiu (Ya’an) Pharmaceutical Company Limited, Ya’an 625000, China;State Key Laboratory Breeding Base of Systematic Research, Development and Utilization of Chinese Medicine, School of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China;State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, Sichuan University, Chengdu 610041, China;

关键词: organocatalysis;    asymmetric synthesis;    one-pot reaction;    multicomponent reaction;    aminocatalysis;    spirocyclic piperidone;   

DOI  :  10.3390/catal7020046

来源: DOAJ

【 摘 要 】

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%.

【 授权许可】

Unknown