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Synfacts 2024; 20(06): 0621
DOI: 10.1055/s-0043-1774853
Polymer-Supported Synthesis

Enantioselective Michael Addition Using Ni(OAc)2−Chiral Covalent Organic Cage Complexes

Contributor(s):
Yasuhiro Uozumi
,
Aya Tazawa
Wang K, Tang X, Anjali BA, Dong J, Jiang J, *, Liu Y, *, Cui Y. * National University of Singapore, Singapore and Shanghai Jiao Tong University, P. R. of China
Chiral Covalent Organic Cages: Structural Isomerism and Enantioselective Catalysis.

J. Am. Chem. Soc. 2024;
146: 6638-6651
DOI: 10.1021/jacs.3c12555
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Key words

chiral covalent organic cages - nickel catalysis - enantioselective Michael addition

Significance

Chiral covalent organic cages (CCOC-1 and 2) were prepared from 5,10-di(3,5-diformylphenyl)-5,10-dihydrophenazine and (1R,2R)-cyclohexanediamine according to equation 1. A CCOC–Ni(OAc)2 complex, generated in situ, promoted the enantioselective Michael addition of 2-acetylazaarenes with E-nitroalkenes in the ­presence of DIPEA to afford the corres­ponding Michael adducts in up to 94% yield with 96:4 er (eq 2).


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Comment

CCOCs were characterized by means of NMR measurements, FT-IR, MALDI-TOF-MS, SEM, XRD, PXRD, XANES, EXAFS and UV/Vis. In the enantioselective Michael addition of 1-(5-chloro-2-pyridinyl)ethenone with E-β-nitrostyrene, the CCOC-2-Ni(OAc)2 complex was recovered and reused four times without significant loss of its catalytic activity and enantioselectivity (5th run; >78% yield, 93:7 er).


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Publication History

Article published online:
14 May 2024

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