103258-06-6

Upstream product

• 20383-28-2 N,N-diisopropyl benzamide 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 350587-39-2 2-(3,4-dimethyl-5-phenyl-oxazolidin-2-yl)-N,N-diisopropyl-benzamide 
• 880152-84-1 C₂₄H₃₂N₂O₂ 
• 227201-73-2 N,N-diisopropyl-2-ethyl-6-formylbenzamide 
• 227201-71-0 N,N-diisopropyl-2-formyl-6-methylbenzamide 
• 1428732-55-1 2-((di-tert-butylphosphino)methyl)-N,N-diisopropylbenzamide hydrobromide 
• 220208-74-2 N,N-diisopropyl-o-allyloxymethylbenzamide 
• 354565-61-0 (2'S,4'S,5'R)-N,N-diisopropyl-2-[3,4-dimethyl-5-phenyl-1,3-oxazolan-2-yl]-6-(methylsulfanyl)benzamide 
• 354565-60-9 2-(3,4-dimethyl-5-phenyl-oxazolidin-2-yl)-6-formyl-N,N-diisopropyl-benzamide 

Relevant academic research and scientific papers

Conformational arm-wrestling: Battles for stereochemical control in benzamides bearing matched and mismatched chiral 2- and 6-substituents

The orientation of a tertiary amide group adjacent to an aromatic ring may be governed by the stereochemistry of an adjacent chiral substituent. With a chiral substituent in both ortho positions, matched/mismatched pairs of isomers result. Evidence for ma

Directed: Ortho-metalation-nucleophilic acyl substitution strategies in deep eutectic solvents: The organolithium base dictates the chemoselectivity

Directed ortho metalation (DoM) or nucleophilic acyl substitution (SNAc) can be efficiently programmed on the same aromatic carboxylic acid amide, in a choline chloride-based eutectic mixture, by simply switching the nature of the organolithium reagent. Telescoped, one-pot ortho-lithiation/Suzuki-Miyaura cross-couplings have also been demonstrated for the first time in Deep Eutectic Solvents.

Phthalide: A direct building-block towards P,O and P,N hemilabile ligands. Application in the palladium-catalysed Suzuki-Miyaura cross-coupling of aryl chlorides

The direct synthesis of new hemilabile ligands from the economical, readily available lactone phthalide is described. Pd-complexes of one such ligand were found highly effective in general Suzuki-Miyaura cross-coupling reactions, including deactivated and hindered aryl chlorides. The Royal Society of Chemistry 2013.

Synthesis of atropisomeric diamides with remotely related stereogenic axes by stereoselective additions to imines

Atroposelective addition of axially chiral laterally lithiated 2-alkyl- 1-naphthamides to 6-substituted 2-(N-methylformimino)benzamides leads, after equilibration of the new stereogenic axis to its more stable conformation, to single atropisomeric diaster

Sparteine-mediated enantioselective [2,3]-Wittig rearrangement of allyl ortho-substituted benzyl ethers and ortho-substituted benzyl prenyl ethers

The (-)-sparteine-mediated enantioselective [2,3]-Wittig rearrangement of N,N-dialkyl-o-allyloxymethylbenzamides and o-substituted benzyl prenyl ethers has been investigated. Enantiomeric excess up to 60% was observed as for the reaction with N,N-diethyl-o-allyloxymetylbenzamide. From the mechanistic investigations, it was suggested that the stereoinformation was introduced at the deprotonation step. Substoichiometric amount of (-)- sparteine (0.2 equiv.) did not decrease the enantioselectivity. Introduction of functional groups other than carbamoyl group did not enhance the enantioselectivity in this rearrangement.

Enantioselective [2,3]-Wittig rearrangement via sparteine-mediated lateral metalation of N,N-dialkyl-o-allyloxymethylbenzamides and o-substituted benzyl prenyl ethers

The (-)-sparteine-mediated enantioselective [2,3]-Wittig rearrangement of N,N-dialkyl-o-allyloxymethylbenzamides and o-substituted benzyl prenyl ethers has been investigated. With N,N-diethyl-o-allyloxymethylbenzamide, enantiomeric excess up to 60% was observed in pentane. These results suggest that the carbamoyl group can effectively assist the transfer of stereoinformation by coordinating with the (-)-sparteine-n-BuLi complex. Other functional groups (OMe, OCONR2, OMOM, F) were impotent to the enantiodifferentiation of this rearrangement.

1-(Dialkylamino)isobenzofurans: Generation and Use for Annelation of Aromatic Rings

Three methods are reported for the generation of the heretofore unreported 1-(dialkylamino)isobenzofurans.These are (1) metal-catalyzed decomposition of an o-(diazomethyl)benzamide (9 to 3), (2) fluoride-induced α elimination of an o-benzamide (48 to 3), and (3) deprotonation of a cyclic imidate salt (51 to 3).The first two reactions are consistent with the intermediacy of a carbene.The precursors for all three approaches can be synthesized from tertiary benzamides by ortho-lithiation strategies.Reaction of the transient 1-(dialkylamino)isobenzofurans with dieneophiles in a ?4s + ?2s cycloaddition is the key step in a one-pot sequence that provides annelation of an aromatic ring by a 2,3-substituted 1-(dialkylamino)-4-hydroxycyclohex-1-ene ring.The sequence of formation of the 1-(dialkylamino)isobenzofuran, regio- and stereospecific cycloaddition, ring opening, and proton transfer, is illustrated by the preparations of 15-23, 32, and 33 from N,N-diisopropylbenzamides.The ring annelation is extended to naphthalene and pyridine rings to provide 40, 41, and 44, respectively.Transformations of annelated products to higher and lower oxidation states are reported.