Synthesis of Morita–Baylis–Hillman-fluorides using 1,1,2,2-tetrafluoroethyl-N,N-dimethylamine
Morita–Baylis–Hillman (MBH)-fluorides are valuable platforms for asymmetric allylic substitution reactions. However, the preparation of MBH-fluorides requires the use of an explosive fluorinating reagent, namely (diethylamino)sulfur trifluoride (DAST). Th
Enantioselective Lewis base catalyzed phosphonyldifluoromethylation of allylic fluorides using a: C -silyl latent pronucleophile
The first enantioselective phosphonyldifluoromethylation is enabled by the use of diethyl (difluoro(trimethylsilyl)-methyl)phosphonate reagent as a latent pronucleophile in the Lewis base catalyzed substitution of allylic fluorides. The reaction proceeds
Zi, You,Lange, Markus,Vilotijevic, Ivan
p. 5689 - 5692
(2020/06/19)
Enantioselective Trichloromethylation of MBH-Fluorides with Chloroform Based on Silicon-assisted C-F Activation and Carbanion Exchange Induced by a Ruppert-Prakash Reagent
Enantioselective trichloromethylation of Morita-Baylis-Hillman (MBH)-type allylic fluorides with chloroform (HCCl3) under organocatalysis was achieved with high to excellent enantioselectivities. Silicon-assisted C-F bond activation by a Rupper
Kinetic resolution of allyl fluorides by enantioselective allylic trifluoromethylation based on silicon-assisted c-F bond cleavage
Two birds, one stone! The first kinetic resolution of allyl fluorides was achieved by the development of an organocatalyzed enantioselective allylic trifluoromethylation. Two kinds of chiral fluorinated compounds, which incorporate C-F and C-CF3 units, respectively, can thus be accessed by a single transformation.
First 1,3-dipolar cycloaddition of Z-α-phenyl-N-methylnitrone with allylic fluorides: A stereoselective route to enantiopure fluorine-containing isoxazolidines and amino polyols
Enantiopure fluorinated isoxazolidines and amino polyols were obtained from the 1,3-dipolar cycloaddition of allylic fluorides and Z-α-phenyl-N- methylnitrone under environment-friendly conditions.