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Lithium 2,3-dihydro-1-benzothiophene-1,1-dioxide: synthesis, characterization, DFT calculations, and reactivity toward aldehydes and azomethines
Tetrahedron ( IF 2.1 ) Pub Date : 5 November 2007 , DOI: 10.1016/j.tet.2007.08.025
Enzo Cadoni , Massimiliano Arca , Stefania De Montis , Claudia Fattuoni , Efisio Perra , Maria G. Cabiddu , Michele Usai , Salvatore Cabiddu

The sulfonyl carbanion derived from 2,3-dihydro-1-benzothiophene-1,1-dioxide and its lithium salt has been investigated by DFT calculations. NMR and IR spectroscopic analyses showed that the lithium sulfonyl carbanion exists in solution as a monomer in equilibrium with a dimer. The lithium carbanion was treated with aldehydes and azomethynes to give chiral hydroxy and amino derivatives. The stereochemistry of the products and the diastereoselectivity of the reaction were investigated.

中文翻译:

2,3-二氢-1-苯并噻吩-1,1-二氧化锂:合成,表征,DFT计算以及对醛和偶氮甲碱的反应性

已经通过DFT计算研究了由2,3-二氢-1-苯并噻吩-1,1-二氧化物衍生的磺酰基碳负离子。NMR和IR光谱分析表明,磺酰锂锂以与二聚体平衡的单体形式存在于溶液中。用醛和偶氮二炔处理碳负离子锂,得到手性羟基和氨基衍生物。研究了产物的立体化学和反应的非对映选择性。
更新日期:2017-01-31
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