92851-01-9Relevant articles and documents
Insights into the diastereoselective control in the sulfa-Michael addition of thiols to nitroalkenes: Stereoelectronic effect in the cyclic chelated transition state
Wang, Jiandong,Li, Pingfan,Yang, Zhanhui,Chen, Ning,Xu, Jiaxi
, p. 370 - 378 (2016)
The diastereoselective control in the sulfa-Michael addition of nitroalkenes and lithium thiolates followed by protonation was investigated. Lithium thiolates first added to nitroalkenes to afford cyclic lithium-chelated nitronates. The subsequent kinetic protonation of nitronates was proved to be the stereochemical determinant through the chelate-controlled six-membered half-chair transition state bearing two approximately 1,2-diaxial substituents due to stereoelectronic effect control. The stereoelectronic effect in the cyclic chelated transition state was probed and verified by tuning the steric bulkiness of the corresponding substituents. The reaction involving 1-nitrocyclohexene provided perfect support for the proposed diastereoselective control model. The current investigation provided not only comprehensive insights into the diastereoselective control in the sulfa-Michael addition of nitroalkenes and thiolates, but also an important role of the stereoelectronic effect in certain organic reactions involving cyclic chelate transition states.
Diastereoselectivity in the triethylamine-catalyzed sulfa-Michael addition of thiols to nitroalkenes: Kinetic and thermodynamic control
Wang, Jiandong,Chen, Ning,Xu, Jiaxi
, p. 4007 - 4014 (2015/06/02)
The diastereoselectivity in the triethylamine-catalyzed sulfa-Michael addition of nitroalkenes and thiols was investigated. The sulfa-Michael addition is kinetic control at the beginning and thermodynamic control at the end for less bulky reactants. Thus,
