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exo-Selective construction of spiro-[butyrolactone-pyrrolidine] via 1,3-dipolar cycloaddition of azomethine ylides with α-methylene-γ-butyrolactone catalyzed by Cu(i)/DTBM-BIPHEP†
Qing-Hua Li,Tang-Lin Liu,Liang Wei,Xiang Zhou,Hai-Yan Tao
Chemical Communications Pub Date : 08/23/2013 00:00:00 , DOI:10.1039/C3CC45493B
Abstract

An expedient access to optically active spiro-[butyrolactone-pyrrolidine] was successfully developed via an unprecedented Cu(I)-catalyzed exo-selective 1,3-DC of azomethine ylides with α-methylene-γ-butyrolactone, which exhibited high diastereoselectivity (>98 : 2), excellent enantioselectivity (96–>99% ee) and a broad substrate scope under mild conditions.

Graphical abstract: exo-Selective construction of spiro-[butyrolactone-pyrrolidine] via 1,3-dipolar cycloaddition of azomethine ylides with α-methylene-γ-butyrolactone catalyzed by Cu(i)/DTBM-BIPHEP
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