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 inOrganic letters Vol. 24; no. 13; pp. 2573 - 2578
Main Authors Chang, Xin, Ran, Jing-Di, Liu, Xue-Tao, Wang, Chun-Jiang
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 08.04.2022
Amer Chemical Soc
Subjects
Amino Acids
antihypertensive agents
Azo Compounds
benzylation
Catalysis
catalysts
catalytic activity
Chemistry
Chemistry, Organic
enantioselectivity
imines
Lewis Acids
palladium
Palladium - chemistry
Physical Sciences
Science & Technology
Stereoisomerism
Thiosemicarbazones
CU/PD CATALYSIS
CARBONATES
ENANTIOSELECTIVE SYNTHESIS
(S)-ALPHA-METHYLDOPA
NUCLEOPHILIC-SUBSTITUTION
ALLYLIC ALKYLATION
ALPHA-AMINO-ACIDS
METAL
INHIBITORS
(R)-ALPHA-METHYLDOPA
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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
1523-7052
DOI:10.1021/acs.orglett.2c00865