Solid supported Hayashi–Jørgensen catalyst as an efficient and recyclable organocatalyst for asymmetric Michael addition reactions |
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Authors: | Piotr Szcze?niak Olga Staszewska-Krajewska Bart?omiej Furman Jacek Mlynarski |
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Institution: | 1. Faculty of Chemistry, Jagiellonian University, Ingardena 3, 30-060 Krakow, Poland;2. Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland |
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Abstract: | A comparison of three different catalytic systems for the efficient, asymmetric synthesis of N-({(3R,4R)-4-(benzyloxy)methyl]pyrrolidin-3-yl}methyl)-N-(2-methylpropyl)benzenesulfonamide 1 (BZN) is described. The presented strategy is based on the organocatalytic Michael addition of aldehyde 2 to trans-nitroalkene 3, and subsequent reductive cyclization. High yields, enantio-, and diastereoselectivities were achieved in the Michael addition by application of a POSS- or Wang resin-supported Hayashi–Jørgensen catalyst. |
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Keywords: | Corresponding author |
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