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Rhodium-Catalyzed Asymmetric 1,4-Addition of α/β-(N-Indolyl) Acrylates
Shuting Tan1, Jian-Guo Liu1, Ming-Hua Xu1,2
1Shenzhen Grubbs Institute and Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen 518055, China.
Abstract:
A rhodium-catalyzed asymmetric 1,4-addition of α/β-(N-indolyl) acrylates to access highly enantioenriched chiral N-alkylindoles promoted by chiral diene or sulfur-olefin ligands under mild reaction conditions has been developed, which provides an efficient and practical approach for constructing carbon stereocenters adjacent to the indole nitrogen. The reaction can be applied to various N-indolyl-substituted α,β-unstaturated esters and arylboron reagents, providing access to a wide range of α- and β-(N-indolyl) propionate derivatives in high yields with excellent enantioselectivities (≤99% ee).
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