Recently, the team led by Associate Professor Wenjun Li from the School of Pharmacyhavemade significant progress in the field of asymmetric organocatalysis. Their research, titled “Organocatalytic Enantioselective 1,12-Addition of Alkynyl Biphenyl Quinone Methides Formed In Situ,” was published in the prestigious international journal Angewandte Chemie International Edition (Angew. Chem. Int. Ed. 2024, DOI: 10.1002/anie.202400143). Our university is the primary institution and corresponding author unit for this work. The first co-authors of the paper are Xing Wang, a master's student from our university (class of 2019), and Boming Shen and Meiwen Liu,PhDstudents from Southern University of Science and Technology. The corresponding authors are Associate Professor Wenjun Li, Professor Pengfei Li, and Professor Peiyuan Yu. This research was funded by the Young Taishan Scholars Program and the Shandong Provincial Natural Science Foundation.

Methine quinones are structural units widely found in bioactive molecules and are key intermediates for synthesizing many natural products. Due to their high reactivity, methine quinones readily react with nucleophiles. Particularly, attacks on the methine position trigger strong re-aromatization, facilitating the synthesis of phenol derivatives with various benzyl substituents. Asymmetric conjugate addition reactions ofortho-methine quinones (o-QMs) orpara-methine quinones (p-QMs) can efficiently achieve stereoselective electrophilic alkylation of α-functionalized alcohols, providing new strategies for constructing complex chiral molecules. However, asymmetric reactions involving methine and carbonyl groups embedded in different aromatic rings are rarely reported.

Basedon previous work (Org. Lett. 2019, 21, 503; Org. Lett. 2019, 21, 7415; Org. Chem. Front. 2020, 7, 3446; Org. Chem. Front. 2021, 8, 3469; Org. Lett. 2022, 24, 4914; Org. Chem. Front. 2023, 10, 3662; Adv. Synth. Catal. 2024, 366, 1078), Wenjun LifromQingdao University, in collaboration with Pengfei Li and Peiyuan Yu from Southern University of Science and Technology, developed an asymmetric 1,12-conjugate addition based on methine biphenyl quinone (4,4'-BQMs) intermediates. This method achieved the asymmetric electrophilic alkylation of 4-(4'-hydroxyphenyl)benzyl alcohol, efficiently and enantioselectively synthesizing a series of axially chiral tetrasubstituted alkenes. This strategy not only enriched the types of α-functionalized alcohols but also expanded asymmetric conjugate addition reactions to stereoselective 1,12-conjugate additions. This research provides new ideas for further in-depth studies in this field.