474433-52-8

Upstream product

• 244-63-3 betacarboline 
• 81171-44-0 1-benzyloxy-1-(trimethylsilyloxy)ethylene 
• 591226-05-0 9-[N-(p-nitrobenzoyl)-(S)-pyroglutamyl]-β-carboline 
• 17341-93-4 2,2,2-Trichloroethyl chloroformate 
• 591226-01-6 9-[N-(benzoyl)-(S)-pyroglutamyl]-β-carboline 
• 591225-99-9 9-(N-acetyl-(S)-pyroglutamyl)-β-carboline 
• 474433-42-6 9-[N-(anthracen-9-ylmethyl)-(S)-pyroglutamyl]-β-carboline 

Downstream Products

• 591225-67-1 1-benzyloxycarbonylmethyl-1,2,3,4-tetrahydro-2-(2,2,2-trichloroethoxycarbonyl)-β-carboline 

Relevant academic research and scientific papers

A general method for the asymmetric synthesis of both enantiomers of 1-substituted 1,2,3,4-tetrahydro-β-carbolines employing pyroglutamic acid derivatives as chiral auxiliaries

9-(S)-Pyroglutaminyl-β-carbolines were allowed to react with a nucleophile (allyltributyltin or a silyl enol ether) in the presence of 2,2,2-trichloroethyl chloroformate to give 1,2-addition products in good yields and high diastereoselectivity. The chiral auxiliary at N-9 was readily removed by a mild hydrolysis. The same chiral source afforded both enantiomers by simply altering a protecting group of the amide nitrogen. That is, (S)-pyroglutaminyl groups which had an N-alkyl group afforded the (S) isomer, whereas the ones having an N-acyl group produced the (R) isomer of the addition products.