磺酰
化学
结合
对映选择合成
硫脲
硝基
加合物
药物化学
催化作用
有机催化
立体化学
有机化学
数学分析
烷基
数学
作者
Michał Kopyt,J. Dudzinski,Michał Barbasiewicz,Piotr Kwiatkowski
标识
DOI:10.1021/acs.orglett.5c00412
摘要
The sulfonyl group is able to polarize adjacent C=C bonds, but strength of the effect considerably varies with sulfonyl substituents (SO2X). In this report, we present asymmetric organocatalyzed conjugate addition of 1,3-dicarbonyl compounds to β-arylvinyl triflones (ArCH=CHSO2CF3). The reaction runs under mild conditions with 5 mol % of tertiary amino-thiourea to afford Michael-type adducts in high yields and enantioselectivities. Comparative experiments reveal that electron-withdrawing properties increase in the series SO2F ≪ SO2CF3 < SO2C4F9, with the latter approaching strength of the nitro group.
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