Enantioselective Ugi and Ugi-azide reactions catalyzed by anionic stereogenic-at-cobalt(III) complexes

Bing-Bing Sun, Kun Liu, Quan Gao, Wei Fang, Shuang Lu, Chun-Ru Wang, Chuan-Zhi Yao, Hai-Qun Cao () and Jie Yu ()
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Bing-Bing Sun: Anhui Agricultural University
Kun Liu: Anhui Agricultural University
Quan Gao: Anhui Agricultural University
Wei Fang: Anhui Agricultural University
Shuang Lu: Anhui Agricultural University
Chun-Ru Wang: Anhui Agricultural University
Chuan-Zhi Yao: Anhui Agricultural University
Hai-Qun Cao: Anhui Agricultural University
Jie Yu: Anhui Agricultural University

Nature Communications, 2022, vol. 13, issue 1, 1-11

Abstract: 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.).

Date: 2022
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DOI: 10.1038/s41467-022-34887-1

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