Unexpected rearrangements and a novel synthesis of 1,1-dichloro-1-alkenones from 1,1,1-trifluoroalkanones with aluminium trichloride

• Beatrice Lansbergen,
• Catherine S. Meister and
• Michael C. McLeod

Beilstein J. Org. Chem. 2021, 17, 404–409, doi:10.3762/bjoc.17.36

• trichloride; dichloroalkenes; Friedel–Crafts alkylation; rearrangement; trifluoroalkanes; Introduction 1,1-Dichloro-1-alkenes are valuable synthetic intermediates and have been employed in Pd-mediated cross couplings of one or both chlorine atoms [1][2][3][4][5][6][7], carbonylation reactions [8], and C–H

Homologated amino acids with three vicinal fluorines positioned along the backbone: development of a stereoselective synthesis

• Raju Cheerlavancha,
• Ahmed Ahmed,
• Yun Cheuk Leung,
• Aggie Lawer,
• Qing-Quan Liu,
• Marina Cagnes,
• Hee-Chan Jang,
• Xiang-Guo Hu and
• Luke Hunter

Beilstein J. Org. Chem. 2017, 13, 2316–2325, doi:10.3762/bjoc.13.228

• trifluoroalkane 40b (Scheme 4) [17]. Trifluoroalkanes 40a and 40b (Scheme 4) were advanced intermediates along the route towards the target trifluorinated amino acids (6). To complete the synthesis, the final requirements were to oxidise the aryl moiety into a carboxylic acid, and to deprotect the amino group

• metaperiodate and ruthenium chloride (Table 2) [39][40], with the desired carboxylic acid 44 being obtained in 31% yield. Having established the conditions necessary for the conversion of the nitroaryl group in model system 41 (Table 2), the procedure could now be applied to the trifluoroalkanes 40a,b (Scheme 4