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Catalysts 2017, 7(2), 46; doi:10.3390/catal7020046

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

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
Received: 14 December 2016 / Revised: 18 January 2017 / Accepted: 22 January 2017 / Published: 4 February 2017
(This article belongs to the Special Issue Metal-free Organocatalysis)
View Full-Text   |   Download PDF [2142 KB, uploaded 4 February 2017]   |  

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
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Liu, Y.; Ouyang, L.; Tan, Y.; Tang, X.; Kang, J.; Wang, C.; Zhu, Y.; Peng, C.; Huang, W. One-Pot Two-Step Organocatalytic Asymmetric Synthesis of Spirocyclic Piperidones via Wolff Rearrangement–Amidation–Michael–Hemiaminalization Sequence. Catalysts 2017, 7, 46.

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