1190763-76-8

Upstream product

• 120-72-9 indole 
• 1122-91-4 4-bromo-benzaldehyde 
• 487-89-8 Indole-3-carboxaldehyde 
• 92206-72-9 4-bromobenzylmagnesium bromide 
• 1554539-59-1 C₁₈H₂₀BrNOSi 

Downstream Products

• 1260909-30-5 3-(4-bromophenyl)-3-(1H-indol-3-yl)-1-phenylpropan-1-one 
• 1293391-61-3 3-(4-bromobenzyl)-1H-indole 
• 1172116-85-6 3-((4-bromophenyl)(1H-indol-3-yl)methyl)-1-methyl-1H-indole 
• 1554539-59-1 C₁₈H₂₀BrNOSi 
• 1360600-14-1 C₃₄H₂₉BrN₂ 

Relevant academic research and scientific papers

Highly Diastereo- and Enantioselective Synthesis of Cyclohepta[b]indoles by Chiral-Phosphoric-Acid-Catalyzed (4+3) Cycloaddition

A highly enantio- and diastereoselective formal (4+3) cycloaddition of 1,3-diene-1-carbamates with 3-indolylmethanols in the presence of a chiral phosphoric acid catalyst is reported. The approach described herein provides efficient access to 6-aminotetrahydrocyclohepta[b]indoles in good yields with mostly complete diastereoselectivity and excellent levels of enantioselectivity (>98:2 dr and up to 98 % ee). Mild reaction conditions, facile scale-up, and versatile derivatization highlight the practicality of this methodology. A mechanistic study suggests that cycloaddition occurs in a stepwise fashion, after the formation of an ion pair between the chiral catalytic phosphate and the intermediate carbocation.

Friedel-Crafts Hydroxyalkylation of Indoles Mediated by Trimethylsilyl Trifluoromethanesulfonate

Indoles and N-alkylindoles undergo Friedel-Crafts addition to aldehydes in the presence of trimethylsilyl trifluoromethanesulfonate and a trialkylamine to produce 3-(1-silyloxyalkyl)indoles. Neutralization of the reaction mixture with pyridine followed by deprotection under basic conditions with tetrabutylammonium fluoride provides the 1:1 adduct as the free alcohol. This method prevents spontaneous conversion of the desired products to the thermodynamically favored bisindolyl(aryl)methanes, a process typically observed when indoles are reacted with aldehydes under acidic conditions.

A highly efficient route to C-3 alkyl-substituted indoles via a metal-free transfer hydrogenation

A highly efficient route to C-3 alkyl-substituted indoles via completely metal-free catalytic transfer hydrogenation of 3-indolemethanols was developed. This process proceeds via vinylogous iminium intermediates formed in situ in the presence of Br?nsted

Enantioselective synthesis of triarylmethanes by chiral imidodiphosphoric acids catalyzed friedel-crafts reactions

The first enantioselective synthesis of pyrrolyl-substituted triarylmethanes has been accomplished using a novel imidodiphosphoric acid catalyst, which is derived from two (R)-BINOL frameworks with different 3,3′-substituents. This strategy was also expanded to the synthesis of bis(indolyl)-substituted triarylmethanes with high enantioselectivities, which could only be obtained with moderate ee values in previous reports. These two efficient Friedel-Crafts alkylation processes feature low catalyst loading, broad functional group compatibilities, and the potential to provide practical pathways for the synthesis of enantioenriched bioactive triarylmethanes.

The direct asymmetric alkylation of α-amino aldehydes with 3-indolylmethanols by enamine catalysis

This work describes an efficient α-alkylation reaction of α-amino aldehydes with 3-indolylmethanols. In the promotion of catalyst 3f, the target products were obtained in high yields (up to 99%), good diastereoselectivities (up to 88:12), and excellent en

Highly enantioselective alkylation reaction of enamides by bronsted-acid catalysis

The H8-BINOL-derived, phosphoric acid catalyzed, highly enatioselective alkylation reaction of enamides with Indoiyl alcohols has been described. A phosphoric acid derived from H8-BINOL enabled an asymmetric α-alkylation of enamides with indoiy