D-Glucose-based azacrown ethers with a phosphonoalkyl side chain: application as enantioselective phase transfer catalysts

…, T Novák, K Ludányi, B Pete, L Tõke, G Keglevich

Index: Bako, Peter; Novak, Tibor; Ludanyi, Krisztina; Pete, Bela; Toke, Laszlo; Keglevich, Gyoergy Tetrahedron Asymmetry, 1999 , vol. 10, # 12 p. 2373 - 2380

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Citation Number: 59

Abstract

Five chiral α-d-glucose-based monoaza-15-crown-5 ethers with a phosphonoalkyl side chain 5a–e have been synthesized. The substituent at the nitrogen atom has a major influence on the cation extraction ability of the azacrown. The new lariat ethers 5a–e show significant asymmetric induction as phase transfer catalysts in the Michael addition of 2- nitropropane to chalcone.