Chinese Journal of Organic Chemistry >
(4S,4'S)-2,2'-(4,6-Dibenzofurandiyl)bis[4,5-dihydro-4-phenyloxazole]-Ni(II) Complexes Catalyzed Highly Enantioselective Nitrile Imine Cycloaddition Reactions
Received date: 2023-11-27
Revised date: 2024-02-27
Online published: 2024-03-28
Supported by
National Natural Science Foundation of China ((22278098); National Natural Science Foundation of China ((21908034); National Natural Science Foundation of China ((22008045); Natural Science Foundation of Heilongjiang Province(LH2021H001); Natural Science Foundation of Heilongjiang Province(LH2023B013)
The Ni(II)-chiral (4S,4'S)-2,2'-(4,6-dibenzofurandiyl)bis[4,5-dihydro-4-phenyloxazole] (DBFOX/Ph)-catalyzed asymmetric 1,3-dipolar cycloadditions of nitrile imines to N-α,β-unsaturated acylpyrazoles was presented. This tactic rendered a facile and feasible route to prepare the optically active tetrasubstituted 5-3,5-dimethylpyrazole acyl dihydropyrazole cycloadducts bearing one or two contiguous stereocenters in good yields (up to 97% yield) with high regioselectivities (100%) and enantioselectivities (up to 97.5% ee). Following that, chiral cycloadducts could be obtained consistently in good chemical yields with excellent enantioselectivities within the gram scale process, additionally, toward five kinds of derivatization reactions like nucleophilic and reduction for further conversion of chiral cycloadducts to related chiral dihydropyrazole derivatives encompassing different substituents.
Xixian Cao , Jun You , Qiye Liu , Bo Liu , Yanchao Yu , Wenju Wu . (4S,4'S)-2,2'-(4,6-Dibenzofurandiyl)bis[4,5-dihydro-4-phenyloxazole]-Ni(II) Complexes Catalyzed Highly Enantioselective Nitrile Imine Cycloaddition Reactions[J]. Chinese Journal of Organic Chemistry, 2024 , 44(7) : 2315 -2332 . DOI: 10.6023/cjoc202311029
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