Solid supported Hayashi–Jørgensen catalyst as an efficient and recyclable organocatalyst for asymmetric Michael addition reactions

Abstract A comparison of three different catalytic systems for the efficient, asymmetric synthesis of N -({(3 R ,4 R )-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–Jorgensen catalyst.