479423-32-0Relevant articles and documents
Disulfonimide-Catalyzed Asymmetric Synthesis of δ-Amino-β-Keto Esters
Wang, Qinggang,List, Benjamin
, p. 807 - 809 (2015)
A chiral disulfonimide-catalyzed asymmetric synthesis of δ-amino-β-keto esters via a vinylogous Mukaiyama-Mannich reaction of the Chan diene with N-Boc imines has been developed. The desired products were obtained in good to excellent yields and enantioselectivities.
Gold-Catalyzed Hydrophenoxylation of Propargylic Alcohols and Amines: Synthesis of Phenyl Enol Ethers
Laserna, Victor,Jeapes Rojas, Catherine,Sheppard, Tom D.
supporting information, p. 4443 - 4447 (2019/06/27)
A practical method for the synthesis of phenyl enol ethers is reported. The combination of a gold(I) catalyst and potassium carbonate selectively mediates the addition of phenols to propargylic alcohols/amines in a chemo-, regio-, and stereoselective fash
Asymmetric Aminalization via Cation-Binding Catalysis
Park, Sang Yeon,Liu, Yidong,Oh, Joong Suk,Kweon, Yoo Kyung,Jeong, Yong Bok,Duan, Mengying,Tan, Yu,Lee, Ji-Woong,Yan, Hailong,Song, Choong Eui
supporting information, p. 1020 - 1025 (2017/12/15)
Asymmetric cation-binding catalysis, in principle, can generate “chiral” anionic nucleophiles, where the counter cations are coordinated within chiral environments. Nitrogen nucleophiles are intrinsically basic, therefore, its use as nucleophiles is often challenging and limiting the scope of the reaction. Particularly, a formation of configurationally labile aminal centers with alkyl substituents has been a formidable challenge due to the enamine/imine equilibrium of electrophilic substrates. Herein, we report enantioselective nucleophilic addition reactions of potassium phthalimides to Boc-protected alkyl- and aryl-substituted α-amido sulfones. In situ generated imines smoothly reacted with the nitrogen nucleophiles to corresponding aminals with good to excellent enantioselectivitiy under mild reaction conditions. In addition, transformation of aminal products gave biologically relevant pyrrolidinone-fused hexahydropyrimidine scaffold with excellent stereoselectivity and good yield.
