Highly diastereoselective and thermodynamically controlled nucleophilic addition of α-fluoro-α-phenylthio-α-phenylsulfonylmethane (FTSM) to aldehydes

• Published in: Tetrahedron Vol. 76; no. 5; pp. 130877 - 130887
• Main Authors: Ye, Wenchao, Zhu, Lingui, Luo, Qinyu, Ni, Chuanfa, Hu, Jinbo
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 31.01.2020; Elsevier
• Subjects: Addition reaction; Chemistry; Chemistry, Organic; Diastereoselective synthesis; Fluorine effect; Nucleophilic fluoroalkylation; Physical Sciences; Science & Technology; Thermodynamic control; Addition reaction; Nucleophilic fluoroalkylation; Diastereoselective synthesis; Thermodynamic control; Fluorine effect; FLUORINATED SULFONES; DI; FLUOROALKYLATION; TRIFLUOROMETHYLATION
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2019.130877

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. [Display omitted] •An unusual thermodynamically controlled nucleophilic addition of a carbanion to aldehydes is developed.•The efficient synthesis of β-fluorinated carbinols with high diastereoselectivity is achieved.•The fluorine substitution not only promotes the addition process, but also improves the diastereoselectivity.