22019-76-7

Upstream product

• 92035-96-6 2,4,6-triethylbenzoic acid 
• 102-25-0 1,3,5-triethylbenzene 
• 91-06-5 2-bromo-1,3,5-triethylbenzene 

Downstream Products

• 3766-68-5 2,4,6-Triethylacetophenon 
• 19957-70-1 2,4,6-triethyl-benzoic acid p-tolyl ester 
• 22679-47-6 2,4,6,2',4',6'-hexaethyl-benzophenone 
• 41214-94-2 2,4,6-triethyl-benzoic acid amide 
• 165897-48-3 2,4,6,2',4',6'-hexaethylbenzil 
• 200354-88-7 N,N-diisopropyl-2,4,6-triethylbenzamide 
• 64712-51-2 Methyl-2,4,6-Triethylthiobenzoat 
• 1286255-51-3 (R)-5-(chloromethyl)-5-phenyl-2-(2,4,6-triethylphenyl)-4,5-dihydrooxazole 
• 67902-79-8 2,4,6-Triethyl-thiobenzoic acid S-(2-hydroxy-2-phenyl-butyl) ester 
• 67902-81-2 2,4,6-Triethyl-thiobenzoic acid S-(2-hydroxy-1-methyl-2-phenyl-ethyl) ester 
• 67902-82-3 2,4,6-Triethyl-thiobenzoic acid S-(1-methyl-2-phenyl-ethyl) ester 
• 64712-67-0 2,4,6-triethyl-benzenecarbothioic acid S-(2-phenylethyl) ester 
• 67902-78-7 (2,4,6-Triethyl-benzoylsulfanyl)-acetic acid 
• 92035-96-6 2,4,6-triethylbenzoic acid 

Relevant academic research and scientific papers

Atroposelectivity in the electrophilic substitution reactions of laterally lithiated and silylated tertiary amides

Lateral lithiation-electrophilic quench of 2-alkyl-1-naphthamides and 2,6-dialkylbenzamides yields products containing an atropisomeric Ar-CO axis and a new stereogenic centre with high (generally >95:5) diastereo-selectivity. With imines as electrophiles, single diastereoisomers containing an atropisomeric axis and two new stereogenic centres are formed. 2,6-Dialkylbenzamides may be functionalised stereoselectively at both the 2- and 6-positions, leading (with imines) to symmetrical compounds bearing 1,7-related stereogenic centres. 2-Alkylbenzamides with only one ortho alkyl group are not atropisomeric at ambient temperature but are functionalised diastereoselectively by lateral lithiation-electrophilic quench at - 78°C. Stabilisation of the atropisomeric products by further lithiation and alkylation proves their diastereoselective formation. The lack of stereospecificity in the fluoride-promoted reaction of a laterally silylated 1-naphthamide with an aldehyde suggests that reported reactions of laterally silylated benzamides may also be controlled by the rotationally restricted amide group.

Remote stereocontrol using rotationally restricted amides: (1,5)-Asymmetric induction

The stereochemical influence of a rotationally restricted amide group extends widely across substituted aromatic amides. Stereogenic centres can be created with high levels of (1,5)-stereocontrol when electrophiles are added to the enolates of 2-ketonaphthamides or to lithiated 2-alkylnaphthamides. Sequential double lateral lithiation of 2,6-dialkylbenzamides can lead to compounds containing (1,5) related stereogenic centres by a process of two-directional asymmetric induction.