196086-92-7

Upstream product

• 1908-61-8 4-bromo[2.2]paracyclophane 
• 100-46-9 benzylamine 
• 123535-94-4 12-nitro-1,4(1,4)-dibenzenacyclohexaphane 
• 1633-22-3 [2.2]Paracyclophan 
• 123439-12-3 4-amino[2.2]paracyclophane 
• 100-39-0 benzyl bromide 
• 380626-41-5 N-tert-butyl-[2.2]paracyclophane-4-ylcarbamate 
• 200504-36-5 Benzyl-tricyclo[8.2.2.2^4,7]hexadeca-1⁽¹³⁾,4,6,10⁽¹⁴⁾,11,15-hexaen-5-yl-carbamic acid tert-butyl ester 

Downstream Products

• 200504-32-1 N-Benzyl-2-phenyl-N-tricyclo[8.2.2.2^4,7]hexadeca-1⁽¹³⁾,4,6,10⁽¹⁴⁾,11,15-hexaen-5-yl-acetamide 
• 200504-30-9 N-Benzyl-3-phenyl-N-tricyclo[8.2.2.2^4,7]hexadeca-1⁽¹³⁾,4,6,10⁽¹⁴⁾,11,15-hexaen-5-yl-propionamide 
• 200504-27-4 N-Benzyl-N-tricyclo[8.2.2.2^4,7]hexadeca-1⁽¹³⁾,4,6,10⁽¹⁴⁾,11,15-hexaen-5-yl-propionamide 

Relevant academic research and scientific papers

Para-Functionalization of N-Substituted 4-amino[2.2]paracyclophanes by Regioselective Formylation

Herein, we report a simple and convenient procedure to prepare para-disubstituted [2.2]paracyclophanes in a straightforward manner. Our approach relies on a regioselective formylation of N-substituted 4-amino[2.2]paracyclophanes, which allows an easy access to a series of products incorporating a reactive aldehyde function para to the electron-donating group. These compounds can be engaged in a variety of orthogonal late-stage derivatization processes involving either the carbonyl group or the amine function, and can serve as precursors to rapidly access more complex paracyclophane derivatives. Control of planar chirality is also possible by performing a kinetic resolution of key racemic intermediates through asymmetric transfer hydrogenation. The formylation can be run on a synthetically useful scale, thus confirming the practical applicability of our method.

Diastereoselective Hartwig-Buchwald reaction of chiral amines with rac-[2.2]paracyclophane derivatives

A Hartwig-Buchwald addition of a variety of chiral amines to rac-4-bromo-[2.2]paracyclophane and rac-trifluoromethanesulfonic acid (4-[2.2]paracyclophane) ester was performed with high diastereoselectivities. Kinetic racemic resolution of the starting materials was achieved, providing a rapid access to enantiomerically enriched 4-bromo-[2.2]paracyclophane and the corresponding enantiomerically pure [2.2]paracyclophane amines. Additionally, the first reaction of a secondary amine with a [2.2]paracyclophane halide was achieved.

N-Methyl- and N-benzyl-4-amino[2.2]paracyclophanes as unique planar chiral auxiliaries

Efficient production of racemic and homochiral N-alkyl-[2.2]paracyclophanes from [2.2]paracyclophane via racemic and homochiral 4-carboxy [2.2]paracyclophane is described, including an excellent procedure for the synthesis of homochiral 4-amino[2.2]paracyclophane. Enolisation followed by electrophilic attack proceeds with diastereoselectivities varying from excellent to modest and the chiral auxiliaries are readily recovered in good yields; the configurational stability of the α-haloamides produced is examined.