Lewis acid-catalyzed asymmetric reactions of β,γ-unsaturated 2-acyl imidazoles

Tengfei Kang, Liuzhen Hou, Sai Ruan, Weidi Cao, Xiaohua Liu () and Xiaoming Feng ()
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Tengfei Kang: Sichuan University
Liuzhen Hou: Sichuan University
Sai Ruan: Sichuan University
Weidi Cao: Sichuan University
Xiaohua Liu: Sichuan University
Xiaoming Feng: Sichuan University

Nature Communications, 2020, vol. 11, issue 1, 1-10

Abstract: Abstract The investigation of diverse reactivity of β,γ-unsaturated carbonyl compounds is of great value in asymmetric catalytic synthesis. Numerous enantioselective transformations have been well developed with β,γ-unsaturated carbonyl compounds as nucleophiles, however, few example were realized by utilizing them as not only nucleophiles but also electrophiles under a same catalytic system. Here we report a regioselective catalytic asymmetric tandem isomerization/α-Michael addition of β,γ-unsaturated 2-acyl imidazoles in the presence of chiral N,N′-dioxide metal complexes, delivering a broad range of optically pure 1,5-dicarbonyl compounds with two vicinal tertiary carbon stereocenters in up to >99% ee under mild conditions. Meanwhile, stereodivergent synthesis is disclosed to yield all four stereoisomers of products. Control experiments suggest an isomerization process involved in the reaction and give an insight into the role of NEt3. In addition, Mannich reaction and sulfur-Michael addition of β,γ-unsaturated 2-acyl imidazoles proceed smoothly as well under the same catalytic system.

Date: 2020
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DOI: 10.1038/s41467-020-17681-9

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