Key Laboratory of Drug-Targeting and Drug Delivery System of the Ministry of Education, West China School of Pharmacy, Sichuan University , Chengdu 610041, China.
Chengdu Institute of Organic Chemistry, Chinese Academy of Sciences , Chengdu 610041, China.
Org Lett. 2016 Feb 19;18(4):872-5. doi: 10.1021/acs.orglett.6b00189. Epub 2016 Feb 8.
An α-regio-, diastereo-, and enantioselective [3 + 2] annulation reaction of Morita-Baylis-Hillman carbonates of isatins and activated alkenes with a bulky electron-withdrawing 1,2-benzoisothiazole 1,1-dioxide or 1,2,3-benzoxathiazine 2,2-dioxide motif is reported, furnishing an array of spirooxindoles (>19:1 dr, up to >99% ee) catalyzed by cinchona-derived tertiary amines. Density functional theory calculation studies have been conducted to elucidate the originality of the α-regioselective annulations.
一种α-区域、非对映选择性和对映选择性的[3+2]环加成反应,涉及到色满-巴利希-希尔曼碳酸盐的靛红和活化的烯烃,带有一个体积庞大的吸电子 1,2-苯并异噻唑 1,1-二氧化物或 1,2,3-苯并恶噻嗪 2,2-二氧化物基序,提供了一系列螺环氧化吲哚(>19:1 dr,高达>99%ee),由金鸡纳衍生的叔胺催化。进行了密度泛函理论计算研究,以阐明α-区域选择性环加成的新颖性。