A chiral organic base catalyst with halogen-bonding-donor functionality: asymmetric Mannich reactions of malononitrile with N-Boc aldimines and ketimines. Issue 31 (29th March 2018)

• Record Type: Journal Article
• Authors: Kuwano, Satoru; Suzuki, Takumi; Hosaka, Yusei; Arai, Takayoshi
• Is Part Of: Chemical communications. Volume 54:Issue 31(2018)
• Page Start: 3847
• Page End: 3850
• Publication Date: 2018-03-29
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c8cc00865e
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : Asymmetric Mannich reactions of malononitrile with various N -Boc imines were developed using a chiral organic base catalyst with halogen-bonding-donor functionality. 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%.