Cu(i)-Catalyzed asymmetric exo-selective synthesis of substituted pyrrolidines via a 1,3-dipolar cycloaddition reaction

An (R)-DM-BINAP/Cu(CH3CN)(4)BF4 complex catalyzed exo-selective asymmetric 1,3-dipolar cycloaddition (1,3-DCA) reaction of imino esters with alpha,beta-unsaturated pyrazoleamides has been developed. A series of highly functionalized pyrrolidines with multiple stereogenic centers were obtained with good yields and diastereoselectivities and excellent enantioselectivities (up to 99% ee).

Automated summary

The exo-selective asymmetric 1,3-dipolar cycloaddition reaction catalyzed by (R)-DM-BINAP/Cu(CH3CN)(4)BF4 complex has led to the synthesis of highly functionalized pyrrolidines with multiple stereogenic centers. The products exhibited good yields, diastereoselectivities, and excellent enantioselectivities, with up to 99% ee.