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Issue 31, 2018
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A chiral organic base catalyst with halogen-bonding-donor functionality: asymmetric Mannich reactions of malononitrile with N-Boc aldimines and ketimines

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Abstract

A chiral organic base catalyst with halogen-bonding-donor functionality has been developed. This quinidine-derived acid/base catalyst smoothly promoted the asymmetric Mannich reaction of malononitrile and various N-Boc imines with up to 98% ee. The cooperative interaction with both substrates was responsible for the high activity that allowed a reduction of the catalyst amount to 0.5 mol%.

Graphical abstract: A chiral organic base catalyst with halogen-bonding-donor functionality: asymmetric Mannich reactions of malononitrile with N-Boc aldimines and ketimines

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Article information


Submitted
01 Feb 2018
Accepted
20 Mar 2018
First published
20 Mar 2018

Chem. Commun., 2018,54, 3847-3850
Article type
Communication

A chiral organic base catalyst with halogen-bonding-donor functionality: asymmetric Mannich reactions of malononitrile with N-Boc aldimines and ketimines

S. Kuwano, T. Suzuki, Y. Hosaka and T. Arai, Chem. Commun., 2018, 54, 3847
DOI: 10.1039/C8CC00865E

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