American Chemical Society
ol500929d_si_002.cif (14.76 kB)

Cyclic Aldimines as Superior Electrophiles for Cu-Catalyzed Decarboxylative Mannich Reaction of β‑Ketoacids with a Broad Scope and High Enantioselectivity

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posted on 2014-05-02, 00:00 authored by Heng-Xia Zhang, Jing Nie, Hua Cai, Jun-An Ma
A novel Cu-catalyzed enantioselective decarboxylative Mannich reaction of cyclic aldimines with β-ketoacids is described. The cyclic structure of these aldimines, in which the CN bond is constrained in the Z geometry, appears to be important, allowing Mannich condensation to proceed in high yields with excellent enantioselectivities. A chiral chroman-4-amine was synthesized from the decarboxylative Mannich product in several steps without loss of enantioselectivity.