Journal
ORGANIC LETTERS
Volume 19, Issue 13, Pages 3676-3679Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b01740
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Funding
- Lanzhou Institute of Chemical Physics
- National Natural Science Foundation of China [21573262]
- Natural Science Foundation of Jiangsu Province [BK20161259]
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A copper-catalyzed asymmetric protoboration of both Z-beta-amidoacrylonitriles and ethyl E-beta-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 alpha-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 alpha-amino boronate esters.
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