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Highly diastereoselective and thermodynamically controlled nucleophilic addition of α-fluoro-α-phenylthio-α-phenylsulfonylmethane (FTSM) to aldehydes
Tetrahedron ( IF 2.1 ) Pub Date : 2019-12-12 , DOI: 10.1016/j.tet.2019.130877
Wenchao Ye , Lingui Zhu , Qinyu Luo , Chuanfa Ni , Jinbo Hu

A thermodynamically controlled and reversible nucleophilic addition of a monofluorinated sulfone, α-fluoro-α-phenylthio-α-phenylsulfonylmethane (FTSM), to aldehydes has been developed, which allows the efficient synthesis of β-fluorinated carbinols with high diastereoselectivity. Control experiments showed that the fluorine substitution not only promotes the addition process, but also improves the diastereoselectivity.



中文翻译:

α-氟-α-苯硫基-α-苯磺酰基甲烷(FTSM)对醛的高度非对映选择性和热力学控制的亲核加成反应

已经开发了一种热力学控制和可逆的亲核加成法,将单氟化砜α--α-苯硫基-α-苯基磺酰甲烷(FTSM)添加到醛中,从而可以高效合成具有高非对映选择性的β-氟化甲醇。对照实验表明,氟取代不仅促进了加成过程,而且提高了非对映选择性。

更新日期:2019-12-13
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