888725-64-2

Upstream product

• 31450-13-2 4-bromo-1,1,1-trifluorobut-2-ene 
• 135821-68-0 (S)-N-benzyl-2,3-O-isopropylidene-glyceraldimine 
• 22323-80-4 (4S)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde 
• 100-46-9 benzylamine 

Downstream Products

• 888725-65-3 (1S,2R)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(trifluoromethyl)butylcarbamate 
• 888725-66-4 benzyl (2R,3S,4R)-1,2-dihydroxy-4-(trifluoromethyl)hexan-3-ylcarbamate 

Relevant academic research and scientific papers

Indium-mediated diastereoselective allylation of D- and L-glyceraldimines with 4-bromo-1,1,1-trifluoro-2-butene: Highly stereoselective synthesis of 4,4,4-trifluoroisoleucines and 4,4,4-trifluorovaline

A practical and efficient route for the stereoselective synthesis of (2R,3S)- and (2S,3R)-4,4,4-trifluoroisoleucines and (2R,3S)-4,4,4- trifluorovaline was developed. Indium-mediated allylation of (R)-N-benzyl-2,3-O-isopropylideneglyceraldimine 7 with 4-bromo-1,1,1-trifluoro- 2-butene 4 gave the desired homoallylic amine 8 in high diastereoselectivity (>95% de) with moderate yield. The Cbz-protected (2R,35)-4,4,4- trifluoroisoleucine 14 and Boc-protected (2R,3S)-4,4,4-trifluorovaline 21 were then readily prepared from 8. In addition, following the same procedure, Cbz-protected (2S,3R)-4,4,4-trifluoroisoleucine 28, the enantiomer of 14, was prepared starting from (S)-N-benzyl-2,3-O-isopropylideneglyceraldimine 24.