315242-19-4Relevant articles and documents
Enantioselective one-pot synthesis of β-sulfonyl ketones and trisubstituted tetrahydrothiophenes via β-elimination/cycloaddition sequence
Xue, Lu,Liu, Yidong,Qin, Wenling,Yan, Hailong
supporting information, p. 1215 - 1218 (2018/02/09)
A mild and efficient enantioselective one-pot synthesis of β-sulfonyl ketones and trisubstituted tetrahydrothiophenes via introducing 1,4-dithiane-2,5-diol to the simple kinetic resolution of β-sulfonyl ketones has been described herein. The one-pot reaction sequence including kinetic resolution and cascade sulfa-Michael/Aldol reaction proceeded successively to afford corresponding sulfonyl ketones and tetrahydrothiophenes with high enantioselectivities (85%–98% ee and 84%–95% ee).
Kinetic Resolution of β-Sulfonyl Ketones through Enantioselective β-Elimination using a Cation-Binding Polyether Catalyst
Li, Liang,Liu, Yidong,Peng, Yang,Yu, Lei,Wu, Xiaoyan,Yan, Hailong
supporting information, p. 331 - 335 (2016/01/25)
Reported herein is the first enantioselective β-elimination reaction catalyzed by a chiral cation-binding polyether. By using this catalytic protocol, a wide range of β-sulfonyl ketones could be effectively resolved with high stereoselectivity (S up to >300). Key to the success of this process is the favorable secondary interactions of the catalyst with the Lewis basic groups on the sulfone substrate. The enone product of this process can be easily converted into the racemic starting material, and allows an effective recycling and overall synthesis of chiral β-sulfonyl ketones in high yield and excellent enantioselectivity.
