Synthesis of Amides with Remote Stereocenters by Catalytic Asymmetric γ-Alkynylation of α,β-Unsaturated Amides.

Abstract

An iridium-catalyzed enantioselective hydroalkynylation of α,β-unsaturated amides was described. The selectivity of this reaction is distinct from that observed in many catalytic hydroalkynylations of α,β-unsaturated carbonyl compounds. It occurs selectively at the γ instead of the β position. Preliminary mechanistic studies suggest that the reaction proceeds through alkene isomerization followed by hydroalkynylation. This method provides a straightforward route for the synthesis of amides with a remote stereocenter at the γ position.

Cite this paper

@article{Wang2016SynthesisOA, title={Synthesis of Amides with Remote Stereocenters by Catalytic Asymmetric γ-Alkynylation of α,β-Unsaturated Amides.}, author={Zi-xuan Wang and Xiao-yan Bai and Han-Chao Yao and Bi-Jie Li}, journal={Journal of the American Chemical Society}, year={2016}, volume={138 45}, pages={14872-14875} }