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


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


One-Pot Two-Step Organocatalytic Asymmetric Synthesis of Spirocyclic Piperidones via Wolff Rearrangement–Amidation–Michael–Hemiaminalization Sequence - Descarga este documento en PDF. Documentación en PDF para descargar gratis. Disponible también para leer online.

1

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

2

State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, Sichuan University, Chengdu 610041, China

3

China Resources Sanjiu Ya’an Pharmaceutical Company Limited, Ya’an 625000, China



These authors contributed equally to this work.





*

Authors to whom correspondence should be addressed.



Academic Editor: Aurelio G. Csákÿ

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%. View Full-Text

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





Autor: Yanqing Liu 1,†, Liang Ouyang 2,†, Ying Tan 3, Xue Tang 1, Jingwen Kang 1, Chunting Wang 2, Yaning Zhu 3, Cheng Peng 1,* and Wei Huang 1,*

Fuente: http://mdpi.com/



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