Enantioselective Ugi and Ugi-azide Reactions Catalyzed by Anionic Stereogenic-at-cobalt(III) Complexes

Overview

Journal Nat Commun

Specialty Biology

Date 2022 Nov 18

PMID 36400776

Authors

Bing-Bing Sun

Kun Liu

Quan Gao

Wei Fang

Shuang Lu

Chun-Ru Wang

Chuan-Zhi Yao

Hai-Qun Cao

Jie Yu

Affiliations

Soon will be listed here.

Abstract

Ugi reactions and related variations are proven to be atom and step-economic strategies for construction of highly valuable peptide-like skeletons and nitrogenous heterocycles. The development of structurally diverse range of novel catalytic systems and the discovery of new approaches to accommodate a broader scope of terminating reagents for asymmetric Ugi four-component reaction is still in high demand. Here, we report a strategy that enables enantioselective Ugi four-component and Ugi-azide reactions employing anionic stereogenic-at-cobalt(III) complexes as catalysts. The key nitrilium intermediates, generated through the nucleophilic addition of isocyanides to the chiral ion-pair which consists of stereogenic-at-cobalt(III) complexes counteranion and a protonated iminium, are trapped by either carboxylic acids or in situ-generated hydrazoic acid, delivering α-acylamino amides and α-aminotetrazoles in good to excellent enantioselectivities (up to 99:1 e.r.).

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