Enantioselective Synthesis of Spiro[1,3-indanedione-tetrahydrothiophene]s by Organocatalytic Sulfa-Michael/Michael Domino Reaction
Enantioselective Synthesis of Spiro[1,3-indanedione-tetrahydrothiophene]s by Organocatalytic Sulfa-Michael/Michael Domino Reaction
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DOI：
10.1002/ejoc.201500837
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发表时间：
2015-10-01
影响因子：
2.8
通讯作者：
Li, Pengfei
中科院分区：
文献类型：
--
作者：
Duan, Jindian;Cheng, Jing;Li, Pengfei
开发了2-亚芳基-1,3-茚满二酮和4-巯基-2-丁烯酸酯之间的有机催化不对称多米诺反应，用于构建手性螺[茚满-1,3-二酮-四氢噻吩]骨架。在叔胺-硫脲有机催化剂存在下，一系列2-亚芳基-1,3-茚满二酮与4-巯基-2-丁烯酸叔丁酯顺利反应，以良好的收率（75-99％）提供手性螺杂环，具有高对映选择性（89-99％ee）和非对映选择性（75.4：24.6 至 97.1：2.9dr）。值得注意的是，官能化的手性螺杂环也可以通过羟醛缩合/磺胺-迈克尔/迈克尔多米诺骨牌反应在一锅中构建，具有类似的高产率和高不对称诱导。
The organocatalytic asymmetric domino reaction between 2-arylidene-1,3-indanediones and 4-mercapto-2-butenoates for the construction of chiral spiro[indane-1,3-dione-tetra-hydrothiophene] skeletons was developed. In the presence of a tertiary amine-thiourea organocatalyst, a series of 2-arylidene- 1,3-indanediones reacted with tert-butyl 4-mercapto-2-butenoate smoothly to furnish chiral spiro heterocycles in good yields (75-99%) with high enantioselectivities (89-99% ee) and diastereoselectivities (75.4:24.6 to 97.1:2.9dr). Notably, functionalized chiral spiro heterocycles were also built in one pot through an aldol condensation/sulfa-Michael/ Michael domino reaction in similarly high yields with high asymmetric induction.