Asymmetric synthesis of trifluoromethylated derivative of ent‐fragransin C1 was reported. The installation of contiguous stereochemistries across the tetrahydrofuran scaffold was achieved through stereocontrolled conjugate addition, aldol reaction, and a protection‐free intramolecular C‐O bond formation (furan ring formation) via chemoselective generation of the benzylic carbocation.
Base-catalyzed diastereodivergent thia-Michael addition of thiols to chiral β-trifluoromethyl-α,β-unsaturated N-acylated oxazolidin-2-ones is reported. By tuning the base-catalyst (i-Pr2NEt, DABCO, or P2-t-Bu), a range of chiral thia-Michael adducts was synthesized in...
The Cover Feature shows the structures of fluorinated furan lignan, namely trifluoromethylated ent‐fragransin C1 and chiral 1,4‐diarylbutanetriol, which is a key intermediate. Using an acid catalyst, chiral trifluoromethylated 1,4‐diarylbutanetriol undergoes chemoselective generation of the benzylic carbocation followed by stereoselective cyclization to provide the furan product with high stereo‐selectivity. The fireworks illustrate the reaction processes and celebrate the accomplishment of the work using “Loi Kratong” festival, one of the famous Thai traditions held in full‐moon night of November, as a background. More information can be found in the Full Paper by D. Soorukram et al.
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