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Molecules 2017, 22(11), 1882;

Recent Advances in the Synthesis of Spiroheterocycles via N-Heterocyclic Carbene Organocatalysis

Antibiotics Research and Re-Evaluation Key Laboratory of Sichuan Province, Sichuan Industrial Institute of Antibiotics, Chengdu University, Chengdu 610052, China
Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences, Chengdu 610041, China
College of Ethnic Medicine, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China
University of Chinese Academy of Sciences, Beijing 100049, China
These authors contributed equally to this work.
Author to whom correspondence should be addressed.
Received: 26 September 2017 / Accepted: 30 October 2017 / Published: 8 November 2017
(This article belongs to the Special Issue Advances in Spiro Compounds)


Spiroheterocycles are regarded as a privileged framework because of their wide distribution in various natural products and synthetic molecules and promising bioactivities. This review focuses on the recent advances in the synthesis of spiroheterocycles by using the strategy of N-heterocyclic carbene (NHC) organocatalysis, and is organized based on the stereoselectivity and the reactive intermediates. According to the stereochemistry, this review was divided into two main parts, covering racemic and enantioselective versions. In each part, we firstly describe the synthetic transformations using nucleophilic Breslow intermediates, and then discuss the reactions that employ electrophilic acylazolium or radical cation intermediates. With those distinct catalytic activation modes of NHC organocatlysis, we expect this synthetic protocol will possibly produce new molecules with structural novelty and complexity, which may warrant further research in the field of drug discovery. View Full-Text
Keywords: spiroheterocycles; N-heterocyclic carbene organocatalysis; diastereoselective synthesis; enantioselective synthesis spiroheterocycles; N-heterocyclic carbene organocatalysis; diastereoselective synthesis; enantioselective synthesis

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Liu, Y.; Zhang, X.; Zeng, R.; Zhang, Y.; Dai, Q.-S.; Leng, H.-J.; Gou, X.-J.; Li, J.-L. Recent Advances in the Synthesis of Spiroheterocycles via N-Heterocyclic Carbene Organocatalysis. Molecules 2017, 22, 1882.

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