Chinese Journal of Organic Chemistry >
Novel Chiral C3-Symmetric Monophosphite Ligands: Synthsis and Catalytic Performance in Asymmetric Hydroformylation and 1,4-Conjugate Addition
Received date: 2016-04-11
Revised date: 2016-06-29
Online published: 2016-08-22
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 20773147, 21073211, 21174155).
A family of the novel chiral helical C3-symmetric monophosphite ligands has been synthesized from axially chiral (R)-or (S)-H8-BINOL and PCl3. The performance of these ligands in asymmetric catalysis was evaluated by the Rh-catalyzed asymmetric hydroformylation of styrene, and the Cu-catalyzed asymmetric 1,4-conjugate addition of diethylzinc to acyclic enones. The catalytic hydroformylation of styrene gave rather high conversion (93%), high regioselectivity (b/n=95/5) and low enantioselectivity[28% ee (R)] using ligand (R)-2 in tetrahydrofuran at room temperature. Under the optimal 1,4-conjugate addition of ZnEt2 to chalcone 3a conditions, eleven acyclic enones 4a~4k were all converted smoothly to the 1,4-adducts with high enantiomeric excess. Using Cu(OTf)2 as catalyst precursor and Et2O as solvent at -20℃, the structure of ligand (R)-3 comprising a partially hydrogenated 2,2'-(1,1'-binaphthyl)-phosphite scaffold and an adamantyl moiety was key factor in improving catalytic activity and the enantioselectivity with up to 98% yield and 72% ee (R). The sense of enantiodiscrimination of the reaction was controlled by the configuration of the diaryl phosphite moieties.
Xing Aiping , Tian Mi , Wang Lailai . Novel Chiral C3-Symmetric Monophosphite Ligands: Synthsis and Catalytic Performance in Asymmetric Hydroformylation and 1,4-Conjugate Addition[J]. Chinese Journal of Organic Chemistry, 2016 , 36(12) : 2912 -2919 . DOI: 10.6023/cjoc201604022
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