TY - JOUR
T1 - A Nickel‐Bisdiamine Porous Organic Polymer as Heterogeneous Chiral Catalyst for Asymmetric Michael Addition to Aliphatic Nitroalkenes
AU - Buendia, Mikkel Burggraaf
AU - Kegnæs, Søren
AU - Kramer, Søren
PY - 2020
Y1 - 2020
N2 - We report a polystyrene‐incorporated chiral nickel(II)‐bisdiamine complex, which is accessible on gram‐scale. This metal complex functions as a heterogeneous catalyst for the enantioselective Michael addition between malonates and aliphatic nitroalkenes, and it provides yields and enantioselectivities on par with homogeneous catalysts. Good functional group tolerance is reported for this reaction. Upon recycling, the catalyst achieves significantly higher TONs than previously reported. We demonstrate scalability to multigram‐scale, compatibility with continuous flow production (4.43 gram), and application to the synthesis of the blockbuster drug Pregabalin. Finally, a new tandem reaction is disclosed.
AB - We report a polystyrene‐incorporated chiral nickel(II)‐bisdiamine complex, which is accessible on gram‐scale. This metal complex functions as a heterogeneous catalyst for the enantioselective Michael addition between malonates and aliphatic nitroalkenes, and it provides yields and enantioselectivities on par with homogeneous catalysts. Good functional group tolerance is reported for this reaction. Upon recycling, the catalyst achieves significantly higher TONs than previously reported. We demonstrate scalability to multigram‐scale, compatibility with continuous flow production (4.43 gram), and application to the synthesis of the blockbuster drug Pregabalin. Finally, a new tandem reaction is disclosed.
U2 - 10.1002/adsc.202000875
DO - 10.1002/adsc.202000875
M3 - Journal article
SN - 1615-4150
VL - 326
SP - 5506
EP - 5512
JO - Advanced Synthesis and Catalysis
JF - Advanced Synthesis and Catalysis
IS - 23
ER -