Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy , Ocean University of China , 5 Yushan Road , Qingdao 266003 , China.
Laboratory for Marine Drugs and Bioproducts & Open Studio for Druggability Research of Marine Natural Products , Pilot National Laboratory for Marine Science and Technology (Qingdao) , 1 Wenhai Road , Aoshanwei, Jimo , Qingdao 266237 , China.
Org Lett. 2019 Jun 7;21(11):3963-3967. doi: 10.1021/acs.orglett.9b01110. Epub 2019 May 17.
A novel catalytic asymmetric dienylation of para-quinone methides with allenoates has been developed. Under mild conditions catalyzed by ( R)-SITCP, various dienylated bisarylmethides were obtained in moderate to good yields (up to 82% yield) and excellent enantioselectivities (90-98% ees). The efficacy and robustness were demonstrated by 27 examples of chiral dienylation products. A plausible mechanism, which involved 1,2 H-shift and umpolung of allenoates, was proposed based on deuterium labeling experiments and previous reports.
发展了一种新型的对醌甲川与丙二烯酸酯的催化不对称二烯丙基化反应。在（R）-SITCP 催化下，在温和条件下，得到了各种二烯基双芳基甲酮，产率中等至良好（高达 82%的产率），对映选择性优异（90-98%ee）。通过 27 个手性二烯化产物的实例证明了其有效性和稳健性。根据氘标记实验和先前的报道，提出了一个可能的机制，涉及丙二烯酸酯的 1,2 H-迁移和反转。
