Copper-Catalyzed Enantioselective Cyclopropanation of Internal Olefins with Diazomalonates

Author: 张明智     Updated: 2018-09-12    Read:

Chao Deng, Hua-Kui Liu, Zhong-Bo Zheng, Lijia Wang,* Xiang Yu, Weihua Zhang,* Yong Tang. Copper-Catalyzed Enantioselective Cyclopropanation of Internal Olefins with Diazomalonates.

Org. Lett. 2017, 19, 5717–5719. (IF2016= 6.579)

    https://pubs.acs.org/appl/literatum/publisher/achs/journals/content/orlef7/2017/orlef7.2017.19.issue-21/acs.orglett.7b02694/20171030/images/medium/ol-2017-02694a_0005.gif

 

The first enantioselective copper catalyzed cyclopropanation of internal olefins with diazomalonates is reported. This process provides a new method for the synthesis of chiral 1,1-cyclopropane diesters. With a chiral bi-side arm bisoxazoline–copper(I) complex, the reaction performed well over a series of substrates, giving the desired products in good yields (up to 95%) and excellent enantioselectivities (90–95% ee).