Synthesis of γ-fluoro-α-amino acids by Claisen rearrangement

Synthesis of α-trifluoromethylated amides by Eschenmoser–Claisen-type rearrangement of allylic alcohols

“…A classical aromatic Claisen rearrangement of the bis-2-fluoroallyl ether of p-diphenol was applied to obtain a fluorinated derivative of the anti-malaria agent Bialamicol [13]. Several different examples of Johnson-Claisen rearrangement of 2-fluoro [14] and 3-fluoroallylic alcohols [15] as well as Ireland-Claisen rearrangement of vinyl fluorides [16] and the Kazmaier variant [17] of this rearrangement using amino acid esters of the fluorinated allylic alcohols [18,19] have been also published. As a result of the above-mentioned rearrangements at the a position a fluorine as well as a trifluoromethyl group.…”

Stereoselective synthesis of (2S,3S,4Z)-4-fluoro-1,3-dihydroxy-2-(octadecanoylamino)octadec-4-ene, [(Z)-4-fluoroceramide], and its phase behavior at the air/water interface

“…Similar effects were observed in compressed monolayers of ethyl ( Z )-2-fluorooctadec-2-enoate [ 29 ] and ethyl (2 E ,4 Z )-4-fluorooctadeca-2,4-dienoate [ 43 ]. Moreover, a very short C–H···F–C distance (2.30 Å) was observed in crystalline state for ( Z )-2-amino-4-fluorododec-4-enecarboxylic acid [ 44 ].…”

Recent progress in the use of fluoroorganic compounds in pericyclic reactions

“…The synthesis of g-fluoro-a-amino acids by a Claisen rearrangement has also been reported. 153 The analogous Claisen rearrangements of vinylic fluorides involving an aromatic oxazole derivative 113 have also been demonstrated. 154 The rearranged product 114 can be hydrolyzed to give 115.…”