α-Regioselective Asymmetric [3 + 2] Annulations of Morita–Baylis–Hillman Carbonates with Cyclic 1-Azadienes and Mechanism Elucidation
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- 作者：Kai-Kai Wang ; Tian Jin ; Xin Huang ; Qin Ouyang ; Wei Du ; Ying-Chun Chen
- 刊名：Organic Letters
- 出版年：2016
- 出版时间：February 19, 2016
- 年：2016
- 卷：18
- 期：4
- 页码：872-875
- 全文大小：416K
- ISSN：1523-7052
文摘
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.