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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| Published in | Organic letters Vol. 24; no. 13; pp. 2573 - 2578 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
08.04.2022
Amer Chemical Soc |
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| Abstract | 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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| AbstractList | 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. 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.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. The synergistic chiral Lewis acid/achiral Pd catalyst system was successfully applied in the enantioselective benzylation of various imine esters, giving a range of alpha-benzyl-substituted alpha-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 alpha-methyl-L-dopa. |
| Author | Chang, Xin Wang, Chun-Jiang Ran, Jing-Di Liu, Xue-Tao |
| AuthorAffiliation | State Key Laboratory of Elemento-organic Chemistry Nankai University Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences |
| AuthorAffiliation_xml | – name: State Key Laboratory of Elemento-organic Chemistry – name: Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences – name: Nankai University |
| Author_xml | – sequence: 1 givenname: Xin surname: Chang fullname: Chang, Xin organization: Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences – sequence: 2 givenname: Jing-Di surname: Ran fullname: Ran, Jing-Di organization: Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences – sequence: 3 givenname: Xue-Tao surname: Liu fullname: Liu, Xue-Tao organization: Engineering Research Center of Organosilicon Compounds & Materials, Ministry of Education, College of Chemistry and Molecular Sciences – sequence: 4 givenname: Chun-Jiang orcidid: 0000-0003-3629-6889 surname: Wang fullname: Wang, Chun-Jiang email: cjwang@whu.edu.cn organization: Nankai University |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/35348342$$D View this record in MEDLINE/PubMed |
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| Keywords | 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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| Snippet | The synergistic chiral Lewis acid/achiral Pd catalyst system was successfully applied in the enantioselective benzylation of various imine esters, giving a... |
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| SubjectTerms | 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 |
| Title | Catalytic Asymmetric Benzylation of Azomethine Ylides Enabled by Synergistic Lewis Acid/Palladium Catalysis |
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