188566-30-5

Upstream product

• 197704-06-6 Trifluoro-acetic acid (R)-2-[(E)-benzyloxycarbonylimino]-3,3,3-trifluoro-1-p-tolylsulfanyl-propyl ester 
• 169137-91-1 [(Z)-2-((R)-Toluene-4-sulfinyl)-1-trifluoromethyl-vinyl]-carbamic acid benzyl ester 
• 676-58-4 methylmagnesium chloride 
• 176756-69-7 (R)-2-<(benzyloxycarbonyl)amino>-2-<(4-methylphenyl)sulfenyl>-3,3,3-trifluoropropanal 

Relevant academic research and scientific papers

Highly stereoselective tandem Pummerer reaction/α-hydroxy imine rearrangement of e.P. β-sulfinylenamines

The highly stereoselective tandem Pummerer reaction/α-hydroxy imine rearrangement of E.P. α-fluoroalkyl-β-sulfinylenamines affording chiral non-racemic fluoropyruvaldehydes N,S-ketals is described.

N-Cbz-Trifluoropyruvaldehyde N,S-ketal: Absolute stereochemistry and addition of Grignard reagents. Highly stereoselective entry to trifluoro analogues of Ephedra alkaloids

The chiral non racemic N-Cbz-trifluoropyruvaldehyde-N,S-ketal 1a (enantiomeric excess up to 74%) is a new trifluoro 3-C building block, which has been reacted with several Grignard reagents, stereoselectively affording the corresponding secondary carbinols 2. The N,S-ketal stereocentre, whose absolute stereochemistry has been determined by X-ray analysis of the α-phenylpropionate 3, is able to provide excellent stereocontrol. Highly stereoselective p-tolylthio group displacement afforded the N-Cbz-phenyl derivative 2d, transformed into trifluoro-norephedrine (S,S)-5 and -ephedrine (S,S)-6.