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Novel Chiral Thiourea Derived from Hydroquinine and l-Phenylglycinol: An Effective Catalyst for Enantio- and Diastereoselective Aza-Henry Reaction.

ABSTRACT: A series of chiral thiourea bearing multiple H-bond donors derived from hydroquinine has been reported. The aza-Henry reaction of isatin-derived ketimines and long-chain nitroalkanes catalyzed by these chiral thioureas can achieve high enantioselectivity (78-99% ee) and excellent diastereoselectivity (up to 99:1). This work is the first report on long-chain nitroalkanes as substrates with excellent diastereoselectivity in metal-free catalytic systems.

SUBMITTER: Wang J

PROVIDER: S-EPMC7931441 | biostudies-literature | 2021 Mar

REPOSITORIES: biostudies-literature

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Novel Chiral Thiourea Derived from Hydroquinine and l-Phenylglycinol: An Effective Catalyst for Enantio- and Diastereoselective Aza-Henry Reaction.

Wang Jingdong J Liu Yuxin Y Wei Zhonglin Z Cao Jungang J Liang Dapeng D Lin Yingjie Y Duan Hai-Feng HF

ACS omega 20210218 8

A series of chiral thiourea bearing multiple H-bond donors derived from hydroquinine has been reported. The aza-Henry reaction of isatin-derived ketimines and long-chain nitroalkanes catalyzed by these chiral thioureas can achieve high enantioselectivity (78-99% ee) and excellent diastereoselectivity (up to 99:1). This work is the first report on long-chain nitroalkanes as substrates with excellent diastereoselectivity in metal-free catalytic systems. ...[more]

PMID: 33681620

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