NDLI: Asymmetric Michael addition reactions of 3-substituted benzofuran-2(3H)-ones to nitroolefins catalyzed by a bifunctional tertiary-amine thiourea.

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Asymmetric Michael addition reactions of 3-substituted benzofuran-2(3H)-ones to nitroolefins catalyzed by a bifunctional tertiary-amine thiourea.

Content Provider	Semantic Scholar
Author	Li, Xin Xue, Xiao-Song Liu, Cong Wang, Bin Tan, Bo‐ Xuan Jin, Jia-Lu Zhang, Yue‐ Yan Dong, Nan
Copyright Year	2012
Abstract	The current work reports an organocatalytic strategy for the asymmetric catalysis of chiral benzofuran-2(3H)-ones bearing 3-position all-carbon quaternary stereocenters. Accordingly, highly enantioselective Michael addition reactions of 3-substituted benzofuran-2(3H)-ones to nitroolefins have been developed by utilizing a bifunctional tertiary-amine thiourea catalyst. The reactions accommodate a number of nitroolefins and 3-substituted benzofuran-2(3H)-ones to give the desired chiral benzofuran-2(3H)-one products with moderate to excellent yields (up to 98%) and moderate to very good selectivities (up to 19 : 1 dr and up to 91% ee). Theoretical calculations using the DFT method on the origin of the stereoselectivity were conducted. The effect of the nitroolefin substituent position on the stereoselectivity of the Michael addition reaction was also theoretically rationalized.
Starting Page	1140
Ending Page	1162
Page Count	23
File Format	PDF HTM / HTML
Alternate Webpage(s)	http://www.rsc.org/suppdata/ob/c1/c1ob06518a/c1ob06518a.pdf
PubMed reference number	22089821v1
Alternate Webpage(s)	https://doi.org/10.1039/c1ob06518a
DOI	10.1039/c1ob06518a
Journal	Organic & biomolecular chemistry
Volume Number	10
Issue Number	2
Language	English
Access Restriction	Open
Subject Keyword	Amine Oxidase (Copper-Containing) Amines Catalysis Ethinyl Estradiol Thiourea tertiary
Content Type	Text
Resource Type	Article

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