105676-90-2

Upstream product

• 27356-91-8 1-benzylcyclopropanecarboxylic acid 
• 108546-99-2 t-butyl 1-benzylcyclopropanecarboxylate 
• 27375-34-4 1-benzyl-cyclopropanecarboxylic acid ethyl ester 
• 100-39-0 benzyl bromide 

Downstream Products

• 1346641-00-6 1-benzyl-N-(4-cyano-2,3,5,6-tetrafluorophenyl)cyclopropanecarboxamide 
• 91132-11-5 1-benzyl-cyclopropanecarboxylic acid amide 
• 1448600-56-3 C₁₇H₁₈BrN 
• 1448600-02-9 N-((1-benzylcyclopropyl)methyl)-N-(2-bromophenyl)-1,1,1-trifluoromethanesulfonamide 
• 1448600-19-8 (1aS,7bS)-1a-benzyl-3-((trifluoromethyl)sulfonyl)-1a,2,3,7b-tetrahydro-1H-cyclopropa[c]quinoline 
• 1448600-35-8 C₁₇H₁₆BrNO 

Relevant academic research and scientific papers

Palladium(II)-Catalyzed highly enantioselective C-H arylation of cyclopropylmethylamines

C-H arylation via a Pd(II)/Pd(IV) catalytic cycle has been one of the most extensively studied C-H activation reactions since the 1990s. Despite the rapid development of this reaction in the past two decades, an enantioselective version has not been reported to date. Herein, we report a Pd(II)-catalyzed highly enantioselective (up to 99.5% ee) arylation of cyclopropyl C-H bonds with aryl iodides using mono-N-protected amino acid (MPAA) ligands, providing a new route for the preparation of chiral cis-aryl-cyclopropylmethylamines. The enantiocontrol is also shown to override the diastereoselectivity of chiral substrates.

Palladium(0)-catalyzed enantioselective C-H arylation of cyclopropanes: Efficient access to functionalized tetrahydroquinolines

Activated: The title reaction proceeds efficiently with 1 mol % of palladium and gives tetrahydroquinolines in excellent enantioselectivities (see scheme). The enantiodiscriminating concerted metalation-deprotonation step occurs via a rare seven-membered palladacycle. The cyclopropyl-substituted tetrahydroquinolines can be regioselectively and enantiospecifically reduced to chiral tetrahydrobenzoazepines. Copyright

Pd(II)-catalyzed enantioselective C-H activation of cyclopropanes

Systematic ligand development has led to the identification of novel mono-N-protected amino acid ligands for Pd(II)-catalyzed enantioselective C-H activation of cyclopropanes. A diverse range of organoboron reagents can be used as coupling partners, and the reaction proceeds under mild conditions. These results provide a new retrosynthetic disconnection for the construction of enantioenriched cis-substituted cyclopropanecarboxylic acids.