期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2015, 期 28, 页码 6130-6134出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201500837
关键词
Asymmetric synthesis; Organocatalysis; Domino reactions; Spiro compounds; Heterocycles
资金
- Startup Fund from South University of Science and Technology of China (SUSTC)
- National Natural Science Foundation of China (NSFC) [21302089]
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.
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