861853-88-5

Upstream product

• 177283-77-1 (4R,5R)-N,N'-dimethoxy-N,N',2,2-tetramethyl-1,3-dioxolane-4,5-dicarboxamide 
• 63126-29-4 (4R,5R)-2,2,N,N,N',N'-hexamethyl-1,3-dioxolane-4,5-dicarboxamide 
• 13139-86-1 4-methoxyphenyl magnesium bromide 

Downstream Products

• 861853-97-6 (4S,5S)-4,5-Bis-[(R)-methoxy-(4-methoxy-phenyl)-methyl]-2,2-dimethyl-[1,3]dioxolane 
• 929217-60-7 (-)-{(4R,5R)-2,2-dimethyl-5-[(R)-2,2,2-trifluoro-1-hydroxy-1-(4-methoxyphenyl)ethyl]-[1,3]dioxolan-4-yl}-(4-methoxyphenyl)methanone 
• 861854-00-4 (1R,2R,3R,4R)-1,4-Dimethoxy-1,4-bis-(4-methoxy-phenyl)-butane-2,3-diol 

Relevant academic research and scientific papers

Enantiopure quaternary α-trifluoromethyl-α-alkoxyaldehydes from L-tartaric acid derived ketoamides

(Chemical Equation Presented) The diastereoselective nucleophilic trifluoromethylation of a range of ketoamides derived from L-tartaric acid has been studied. TMSCF3 in the presence of a catalytic amount of K 2CO3 in DMF has been identified as the conditions leading to the highest diastereoselectivities. A sequential one-pot reaction trifluoromethylation-etherification of the trifluoromethylcarbinol has been developed. Only one further one-pot reaction, ketal hydrolysis-oxidative cleavage, led to the final α-trifluoromethylated α-alkoxy-aldehydes. This procedure was applied to the preparation of a series of enantiopure aryl, heteroaryl, and alkyl α-trifluoromethyl-α-alkoxyaldehydes.

Synthesis of enantiopure trifluoromethyl building blocks via a highly chemo- and diastereoselective nucleophilic trifluoromethylation of tartaric acid-derived diketones

(Chemical Equation Presented) A highly diastereoselective nucleophilic mono(trifluoromethylation) of a tartaric acid-based diketone, using trifluoromethyl(trimethyl)silane, afforded the corresponding γ-keto trifluoromethylcarbinol. The scope and limitation of this reaction was studied. The acidic removal of the acetonide moiety protecting the two hydroxyl groups of the adducts was unsuccessful. Bis(O-methylation) of the aromatic derivatives under basic conditions, followed by acidic hydrolysis and oxidative cleavage, led to two different enantiopure products: an α-aryl-α-methoxy- α-trifluoromethyl ethanal and an α-aryl-α-methoxycarboxylic acid. The overall process is eventually an interesting way to convert one natural chiral raw material into two functionalized enantiopure building blocks including a trifluoromethyl one.

Nucleophilic addition reactions of 1,4-diketones derived from tartaric acid: Synthesis of TADDOL analogues

A systematic investigation of the reduction and Grignard reagents addition to 1,4-diketones derived from tartaric acid was carried out. It was found that the reduction proceeded with high selectivity using K-Selectride as the reducing agent; while Grignar

Asymmetric synthesis of α-methoxyarylacetic acid derivatives

Stereoselective synthesis of a series of 2-aryl-2-methoxyethanols was achieved from inexpensive chiral pool tartaric acid employing a diastereoselective reduction of a symmetrical 1,4-diaryldiketone as the key step. 2-Aryl-2-methoxyethanols were enantioselectively prepared in 80-90% yield