140404-39-3

Upstream product

• 165801-06-9 (R)-2-benzyloxy-3,3,3-trifluoropropanol 
• 186581-53-3 diazomethane 
• 100-39-0 benzyl bromide 
• 140461-90-1 (1'R)-2-<1'-(2',2',2'-trifluoro-1'-hydroxyethyl)>-5-(trimethylsilyl)furan 
• 165801-12-7 (2'R,4R)-3-(2'-benzyloxy-3',3',3'-trifluoropropionyl)-4-isopropyl-2-oxazolidinone 
• 154878-15-6 (R)-3-(2-benzyloxyacetyl)-4-isopropyl-2-oxazolidinone 

Relevant academic research and scientific papers

Development of a Novel Pathway To Access 6-Deoxy-6,6,6-trifluorosugars via 1,2-Migration of a tert-Butyldimethylsilyl Group

Trifluoromethylated furanols 2 were enzymatically resolved into the corresponding optically active forms in a highly efficient manner and were further converted to the synthetically useful 2-butenolides 6.Introduction of substituents into these butenolides 6 or their saturated lactone forms 8 was realized by boron trifluoride-mediated Michael addition of cuprates or by capture of the enolates with various kinds of electrophiles, respectively, both of which proceeded with a high degree of diastereoselectivity.Moreover, novel synthetic routes to access 6-deoxy-6,6,6-trifluorosugars were developed by utilization of 1,2-silyl migration as a key step, which was qualitatively supported by PM3 molecular orbital calculation.

Diastereoselective trifluoromethylation of chiral imide enolates with iodotrifluoromethane mediated by triethylborane

The trifluoromethylation of lithium enolates of chiral N-acyloxazolidinones with iodotrifluoromethane mediated by triethylborane proceeds with good diastereomeric excess.

Chiral Trifluoromethylated 2-Butenolides for the Construction of 6-Deoxy-6,6,6-trifluorosugars

Optically active 2-butenolides with a trifluoromethyl (CF3) group are synthesized via enzymatic optical resolution and are selectively transformed into 6,6,6-trifluororhodinose and amicetose by base-promoted 1,2-migration of a tert-butyldimethylsilyl moiety in a highly efficient manner.