Copper-Catalyzed Stereoselective [4 + 2] Cycloaddition of β,γ-Unsaturated α-Keto Esters and 2-Vinylpyrroles in Water.

Org Lett

Hefei National Research Center for Physical Sciences at Microscale, CAS Key Laboratory of Soft Matter Chemistry, and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China.

Published: June 2022

An asymmetric [4 + 2] cycloaddition of β,γ-unsaturated α-keto esters with 2-vinylpyrroles in water was developed under the catalysis of a kind of copper complex with a low loading. A series of optically pure 3,4-dihydro-2-pyran derivatives could be obtained in excellent yields, with high diastereoselectivities and enantioselectivities. The corresponding mechanism was proposed, which was supported by DFT calculations.

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http://dx.doi.org/10.1021/acs.orglett.2c01544DOI Listing

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