Memory of Chirality (MOC) in Intramolecular sp3 C–H Amination

Yucheng Mu; Chendan Zhu; Zhuangzhi Shi

doi:10.1055/s-0035-1560960

Synlett, Inhaltsverzeichnis

Synlett 2016; 27(04): 486-492
DOI: 10.1055/s-0035-1560960

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Memory of Chirality (MOC) in Intramolecular sp³ C–H Amination

Yucheng Mu

State Key Laboratory of Coordination Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, P. R. of China eMail: shiz@nju.edu.cn

,

Chendan Zhu

State Key Laboratory of Coordination Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, P. R. of China eMail: shiz@nju.edu.cn

,

Zhuangzhi Shi*

State Key Laboratory of Coordination Chemistry, Collaborative Innovation Center of Chemistry for Life Sciences, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, P. R. of China eMail: shiz@nju.edu.cn

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Abstract

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Abstract

‘Memory of chirality’ (MOC) is an important concept for the development of efficient asymmetric transformations. However, the phenomenon of MOC in C–H functionalization is still rare. In the past decades, three types of intramolecular C–H amination involving C–H insertion of metal nitrenoids, 1-aza-2-azoniaallene salts, and benzamides to construct N-heterocyclic compounds have been developed in Du Bois, Brewer, and our group, respectively. In these reactions, the formation of a C–N bond does not result in the loss of stereochemical information at the stereogenic center. Here, we discuss the scope, mechanism, and application of these transformations and provide a perspective on the development of this field in future.

Key words

memory of chirality - asymmetric synthesis - N-heterocycles - amination - C–H functionalization

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