570368-31-9

Upstream product

• 14402-93-8 dipentylzinc 
• 570368-30-8 (1R,2Z)-1-methyl-3-phenyl-2-butenyl 2,3,4,5,6-pentafluorobenzoate 
• 570368-28-4 (1R,2E)-1-methyl-3-phenyl-2-butenyl 2,3,4,5,6-pentafluorobenzoate 
• 864777-98-0 (2S,3E)-4-phenylpent-3-en-2-yl 2,6-difluorobenzoate 
• 570368-41-1 (2R,3E)-4-iodo-4-phenyl-3-buten-2-ol 
• 124006-49-1 (2R,3E)-4-phenyl-3-penten-2-ol 
• 363598-97-4 (2R,3Z)-4-phenyl-3-penten-2-ol 
• 285566-28-1 (3E)-4-phenyl-3-penten-2-ol 
• 827-69-0 (E)-4-phenyl-3-penten-2-one 
• 363598-96-3 (2S,3E)-4-phenylpent-3-en-2-ol 

Downstream Products

• 864778-41-6 (2S)-2-phenylheptan-2-yl formate 
• 864778-27-8 (2S)-2-methyl-2-phenylheptanoic acid 
• 570368-32-0 (2S)-2-methyl-2-phenylheptanal 

Relevant academic research and scientific papers

Highly enantioselective preparation of tertiary alcohols and amines by copper-mediated diastereoselective allylic SN2′ substitutions

(Chemical Equation Presented) Trisubstituted allylic pentafluorobenzoates react with diorganozinc reagents in the presence of CuCN·2 LiCl to provide alkenes bearing a chiral quaternary center in α position (> 95 % ee). These alkenes are readily converted into chiral tertiary alcohols or into chiral amino alcohols by a straightforward sequence of ozonolysis followed by Curtius rearrangement (see scheme).

Highly stereoselective anti SN2′ substitutions of (Z)-allylic pentafluorobenzoates with polyfunctionalized zinc-copper reagents

(Matrix presented) Allylic substitution reactions of zinc-copper organometallics on (Z)-allylic pentafluorobenzoates proceed with very high regioselectivity and excellent anti selectivity. The high fidelity in transfer of stereochemical information allowed a short synthesis of (+)-ibuprofen (97% ee).