Abstract
The asymmetric reduction of N-unsubstituted β-enamino esters is the key step for catalytic asymmetric construction of sitagliptin, a prevalent drug for the treatment of type 2 diabetes. However, it is still lack of environment friendly, low-cost, nontoxic, and highly selective catalysts. Herein, we report a series of new silyl ether substituted l-pipecolinic formamides organocatalysts for the asymmetric reduction of N-unsubstituted β-enamino esters with trichlorosilane as the reducing agent. The steric hindrance of silyl ether substitutes can remarkably influence the catalytic performance. The optimized triphenylsilyl substituted catalyst 2k can efficiently catalyze the reduction reaction, affording enantioenriched β-amino ester with excellent yield (95 %) and high ee (82 %).
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