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Cobalt-Catalyzed Regio- and Enantioselective Allylic Alkylation of Malononitriles

Samir Ghorai, Sajid Ur Rehman, Wen-Bin Xu, Wen-Yu Huang and Changkun Li*

* School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, 800 Dongchuan Road, Shanghai 200240, China, Email: chklisjtu.edu.cn

S. Ghorai, S. U. Rehman, W.-B. Xu, W.-Y. Huang, C. Li, Org. Lett., 2020, 22, 3519-3523.

DOI: 10.1021/acs.orglett.0c00962 (free Supporting Information)


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Abstract

A cobalt-catalyzed enantioselective allylic alkylation of malononitriles with allylic carbonates provides chiral γ,δ-unsaturated malononitriles with >20:1 branched/linear regioselectivity and up to 99% enantiomeric excess under mild reaction conditions. The ligand is essential to realize the high reactivity in the carbon-carbon bond formation process.


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Key Words

allylation of active methylene compounds, nitriles


ID: J54-Y2020