1366421-71-7

Upstream product

• 6262-42-6 1,2,3,3-tetrachlorocyclopropene 
• 2627-86-3 (S)-1-phenyl-ethylamine 
• 101-83-7 N-cyclohexyl-cyclohexanamine 

Downstream Products

• 1366421-73-9 (S)-N₁,N₁,N₂,N₂-tetracyclohexyl-3-(1-phenylethylimino)cycloprop-1-ene-1,2-diamine 

Relevant academic research and scientific papers

Enantioselective Bronsted base catalysis with chiral cyclopropenimines

Cyclopropenimines are shown to be a highly effective new class of enantioselective Bronsted base catalysts. A chiral 2,3-bis(dialkylamino) cyclopropenimine catalyzes the rapid Michael reaction of a glycine imine substrate with high levels of enantioselectivity. A preparative scale reaction to deliver 25 g of product is demonstrated, and a trivial large scale synthesis of the optimal catalyst is shown. In addition, the basicity of a 2,3-bis(dialkylamino)cyclopropenimine is measured for the first time and shown to be approximately equivalent to the P1-tBu phosphazene base. An X-ray crystal structure of the protonated catalyst is shown along with a proposed mechanistic and stereochemical rationale.

CYCLOPROPENIMINE CATALYST COMPOSITIONS AND PROCESSES

The present invention provides, inter alia, a cyclopropenimine Br?nsted base catalyst and a cyclopropenimine scaffold for use as a Br?nsted base catalyst. This cyclopropenimine has the structure (100). Methods for making such a cyclopropenimine are also provided. Further provided are processes for carrying out an organic synthetic reaction and processes for catalyzing a proton transfer reaction enantioselectively using such a cyclopropenimine Br?nsted base catalyst.