Enantioselective Synthesis of Cα-Tetrasubstituted N-Hydroxyl-α-amino Nitriles via Cyanation of Ketonitrones Using Me2(CH2Cl)SiCN

Autor: Jin-Sheng Yu, Yu-Fei Ao, Chen Chen, Jian Zhou, Peng-Wei Xu, Xiao-Yuan Cui, Feng Zhou
Rok vydání: 2021
Předmět:
Zdroj: Organic Letters. 23:8471-8476
ISSN: 1523-7052
1523-7060
DOI: 10.1021/acs.orglett.1c03176
Popis: Here, we report an unprecedented catalytic enantioselective cyanation of ketonitrones enabled by the bifunctional cyanating reagent Me2(CH2Cl)SiCN. This approach allows facile access to optically active N-hydroxyl-α-amino nitriles that are of high synthetic value but difficult to acquire by other methods. The use of bifunctional cyanating reagent Me2(CH2Cl)SiCN not only achieves an enantioselectivity higher than that with TMSCN but also enables various diversification reactions of the resulting silylated adducts. This represents the first enantioselective catalytic nucleophilic addition reaction of unactivated ketone-derived nitrones, exhibiting the potential of such tetrasubstituted C═N bonds for asymmetric synthesis of N-hydroxy α-amino acids and other N-hydroxy tertiary amines.
Databáze: OpenAIRE