An efficient Fe(III)-catalyzed 1,6-conjugate addition of para-quinone methides with fluorinated silyl enol ethers toward β,β-diaryl α-fluorinated ketones

• Published in: Tetrahedron Vol. 74; no. 52; pp. 7395 - 7398
• Main Authors: Hao, Yong-Jia, Hu, Xiao-Si, Yu, Jin-Sheng, Zhou, Feng, Zhou, Ying, Zhou, Jian
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 27.12.2018; Elsevier
• Subjects: 1,6-Conjugate addition; Chemistry; Chemistry, Organic; Fe(OTf)3; Fluorinated silyl enol ethers; Physical Sciences; Science & Technology; β,β-diaryl α-fluorinated ketones; 1,6-Conjugate addition; β,β-diaryl α-fluorinated ketones; Fe(OTf)3; Fluorinated silyl enol ethers; ASYMMETRIC FLUORINATION; beta,beta-diaryl alpha-fluorinated ketones; ENANTIOSELECTIVE SYNTHESIS; ONE-POT SYNTHESIS; MUKAIYAMA-MANNICH REACTION; HIGHLY EFFICIENT; ALDOL REACTION; Fe(OTf); TRIFLUOROMETHYL KETONES; ORGANOFLUORINE-ORGANOSILICON CHEMISTRY; TERTIARY AMINE CATALYSIS; DIFLUOROENOL SILYL
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2018.11.017

Reported here is a highly efficient 1,6-conjugate addition of fluorinated silyl enol ethers to para-quinone methides, allowing facile access to a range of β,β-diaryl α-fluorinated ketones with good to high yields. Fe(OTf)3 was identified as the optimal catalyst, with the loading of 3 mol%. Notably, this represent the first 1,6-conjugate addition with fluorinated silyl enol ethers. The synthetic potential of the resulting adducts is also demonstrated. [Display omitted]