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A Nickel‐Bisdiamine Porous Organic Polymer as Heterogeneous Chiral Catalyst for Asymmetric Michael Addition to Aliphatic Nitroalkenes
Author(s) -
Buendia Mikkel B.,
Kegnæs Søren,
Kramer Søren
Publication year - 2020
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202000875
Subject(s) - chemistry , enantioselective synthesis , catalysis , michael reaction , nickel , tandem , organic chemistry , polystyrene , combinatorial chemistry , polymer , materials science , composite material
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.