Catalytic Asymmetric Benzylation of Azomethine Ylides Enabled by Synergistic Lewis Acid/Palladium Catalysis

Catalytic Asymmetric Benzylation of Azomethine Ylides Enabled by Synergistic Lewis Acid/Palladium Catalysis

The synergistic chiral Lewis acid/achiral Pd catalyst system was successfully applied in the enantioselective benzylation of various imine esters, giving a range of α-benzyl-substituted α-amino acid derivatives in satisfactory yield with excellent enantioselectivity. It is worth noting that this str...

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Bibliographic Details
Published in:Organic letters Vol. 24; no. 13; pp. 2573 - 2578
Main Authors: Chang, Xin, Ran, Jing-Di, Liu, Xue-Tao, Wang, Chun-Jiang
Format: Journal Article
Language:English
Published: United States American Chemical Society 08-04-2022
Subjects:
Amino Acids
Azo Compounds
Catalysis
Lewis Acids
Palladium - chemistry
Stereoisomerism
Thiosemicarbazones
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Summary:The synergistic chiral Lewis acid/achiral Pd catalyst system was successfully applied in the enantioselective benzylation of various imine esters, giving a range of α-benzyl-substituted α-amino acid derivatives in satisfactory yield with excellent enantioselectivity. It is worth noting that this strategy exhibits good tolerance for bicyclic and monocyclic benzylic electrophiles. Furthermore, the utility of this synthetic protocol was demonstrated by the expedient preparation of enantioenriched antihypertensive drug α-methyl-l-dopa.
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c00865