Organic Letters
Organic Letters
5 years ago

Copper-Catalyzed Asymmetric Protoboration of β-Amidoacrylonitriles and β-Amidoacrylate Esters: An Efficient Approach to Functionalized Chiral α-Amino Boronate Esters

Copper-Catalyzed Asymmetric Protoboration of β-Amidoacrylonitriles and β-Amidoacrylate Esters: An Efficient Approach to Functionalized Chiral α-Amino Boronate Esters
Senmiao Xu, Haonan Zhao, Xiaoliang Zou, Lili Chen
A copper-catalyzed asymmetric protoboration of both Z-β-amidoacrylonitriles and ethyl E-β-amidoacrylates using bis(pinacolato)diboron has been developed for the first time. The process tolerates a vast array of substrates, delivering a series of stable functionalized chiral α-amino boronate esters in good yields and enantioselectivities under mild reaction conditions. The current method is also applicable for gram-scale synthesis without erosion of enantioselectivity. This work provides an attractive and complementary approach to synthesizing enantioriched chiral α-amino boronate esters.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b01740

DOI: 10.1021/acs.orglett.7b01740

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