218271-90-0

Upstream product

• 177283-77-1 (4R,5R)-N,N'-dimethoxy-N,N',2,2-tetramethyl-1,3-dioxolane-4,5-dicarboxamide 
• 6921-34-2 benzylmagnesium chloride 

Downstream Products

• 218272-12-9 (3aS,4S,8R,8aS)-4,5,7,8-Tetrabenzyl-2,2-dimethyl-hexahydro-1,3-dioxa-5,7-diaza-azulen-6-one 
• 218272-01-6 (4S,5S,6S,7R)-1,3,4,7-Tetrabenzyl-5,6-dihydroxy-[1,3]diazepan-2-one 
• 218272-00-5 (3aS,4R,8S,8aS)-4,8-Dibenzyl-2,2-dimethyl-hexahydro-1,3-dioxa-5,7-diaza-azulen-6-one 
• 218271-94-4 (S)-1-[(4S,5S)-5-((S)-1-Amino-2-phenyl-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-phenyl-ethylamine 
• 218271-99-9 (R)-1-[(4S,5S)-5-((S)-1-Amino-2-phenyl-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-phenyl-ethylamine 
• 218271-92-2 (3S,4S)-2,5-bis(methoxyimino)-1,6-diphenyl-3,4-O-isopropylidenehexanediol 

Relevant academic research and scientific papers

Selective addition of Grignard reagents to 2,3-O-isopropylidene bis-Weinreb tartaric acid amide

Controlled addition of Grignard reagents to tartaric acid derived bis-Weinreb amide 3 provides a facile, direct entry to desymmetrized 1,4-functionalized-syn-2,3-diol intermediates 4 and to C2-symmetrical 1,4-diketones 5. The synthetic versatil

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.