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Regio- and stereoselective syntheses of chiral α-quaternary (Z)-trisubstituted allylic amino acids via synergistic Pd/Cu catalysis.

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Synergistic palladium/copper catalysis for asymmetric allylic alkylation of vinylethylene carbonates with aldimine esters has been developed for the synthesis of α-quaternary (Z)-trisubstituted allylic amino acids under mild conditions. This methodology… Click to show full abstract

Synergistic palladium/copper catalysis for asymmetric allylic alkylation of vinylethylene carbonates with aldimine esters has been developed for the synthesis of α-quaternary (Z)-trisubstituted allylic amino acids under mild conditions. This methodology features broad substrate compatibilities in yields of up to 87% and up to 94% ee. A facile scale-up and straightforward conversion to 1,2,3,5-tetrasubstituted pyrrole and 1,2,5,6-tetrahydropyridine bearing chiral quaternary carbon centers verifies the synthetic utility of this method.

Keywords: quaternary trisubstituted; amino acids; catalysis; allylic amino; chiral quaternary; trisubstituted allylic

Journal Title: Chemical communications
Year Published: 2023

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