139199-72-7

Upstream product

• 61925-49-3 (S)-nonan-3-ol 
• 20445-33-4 (R)-methoxytrifluoromethylphenylacetyl chloride 
• 185019-15-2 nonan-3-ol 
• 20445-31-2 R-(+)-α-trifluoromethyl-α-methoxy-phenylacetic acid 

Relevant academic research and scientific papers

Novel C2-symmetric chiral O,N,N,O-tetradentate 2,2-bipyridyldiolpropane ligands: Synthesis and application in asymmetric diethylzinc addition to aldehydes

First synthesis of C2-symmetric chiral O,N,N,O-tetradentate 2,2-bipyridyldiolpropane ligands is described. The Mukaiyama-Michael reaction was applied as an important reaction for the synthesis of 2,2-bipyridylpropane 9. Among the ligands synthesized, ligand 11 exhibits excellent chiral induction (up to 97% ee) in diethylzinc addition to various aldehydes. The use of additional Lewis acid such as Ti(OiPr)4 in diethylzinc addition reaction is not required for the present catalytic system.

Synthesis of chiral pyridylphenols for the enantioselective addition of diethylzinc to aldehydes

Chiral 8-substituted 2-(8,10,10-trimethyl-6-aza-tricyclo[7.1.1.0 2,7]undeca-2(7),3,5-trien-5-yl)-phenols were prepared from a high enantiopurity (>97% ee) of (1R)-(+)-α-pinene, and assessed in the enantioselective addition of diethylzinc to substituted benzaldehydes, giving the (S)-alcohols with enantiomeric excess ranging from 33% to 89%. Interestingly, in all cases, except for those of ortho-chlorobenzaldehyde, ortho- and para-methoxybenzaldehydes, the ee was >71%. The plot of the Hammett substitution constants vs. enantiomeric excess of the diethylzinc addition to either the ortho- or para-substituted benzaldehydes shows a linear correlation.

Enantioselective transfer hydrogenation of aliphatic ketones catalyzed by ruthenium complexes linked to the secondary face of β-cyclodextrin

Ruthenium-η-arene complexes attached to the secondary face of β-cyclodextrin catalyze the enantioselective reduction (ee up to 98%) of aliphatic and aromatic ketones in aqueous medium in the presence of sodium formate (HCOONa).