174621-92-2

Upstream product

• 108-24-7 acetic anhydride 
• 95798-22-4 3-hydroxy-piperidine-1-carboxylic acid benzyl ester 
• 3742-91-4 N-(benzyloxycarbonyl)piperidine 
• 64-19-7 acetic acid 
• 68471-58-9 1-(benzyloxycarbonyl)-1,2,3,4-tetrahydropyridine 
• 501-53-1 benzyl chloroformate 
• 6859-99-0 3-hydroxypiperazine 

Downstream Products

• 167112-99-4 (S)-3-acetoxy-1-(benzyloxycarbonyl)piperidine 
• 100858-34-2 benzyl (3R)-3-hydroxypiperidine-1-carboxylate 

Relevant academic research and scientific papers

β-Functionalization of Saturated Aza-Heterocycles Enabled by Organic Photoredox Catalysis

The direct β-functionalization of saturated aza-heterocycles has remained a synthetic challenge because of the remote and unactivated nature of β-C-H bonds in these motifs. Herein, we demonstrate the β-functionalization of saturated aza-heterocycles enabl

Direct catalytic anti-markovnikov addition of carboxylic acids to alkenes

A direct catalytic anti-Markovnikov addition of carboxylic acids to alkenes is reported. The catalyst system is comprised of the Fukuzumi acridinium photooxidant (1) and a substoichiometric quantity of a hydrogen-atom donor. Oxidizable olefins, such as styrenes, trisubstituted aliphatic alkenes, and enamides, can be employed along with a variety of carboxylic acids to afford the anti-Markovnikov addition adducts exclusively. A deuterium-labeling experiment lends insight to the potential mechanism.

Lipase-catalyzed practical synthesis of (R)-1-benzyl-3-hydroxy-2,5-pyrrolidinedione and its related compounds

A practical method for preparing (R)-1-benzyl-3-hydroxy-2,5-pyrrolidinedione (1) was investigated by the use of the enzymatic hydrolysis of its acetate (2a). Among several hydrolases examined here, lipase PS from Pseudomonas cepacia gave the best result: In a mixed solvent (1:1 v/v) of dioxane and a phosphate buffer (pH 7), the hydrolysis took place smoothly with a high enantioselectivity (E > 3000). Several 3-alkanoyl derivatives of 1 were subjected to the lipase PS-catalyzed hydrolysis. The chain length of the alkanoyl does not noticeably influence the reaction rate or the enantioselectivity. In contrast, the hydrolysis of the 1-benzoyl derivative proceeded slowly with a low enantioselectivity (E = 19). The syntheses of optically active 3-hydroxypyrrolidines and 3-hydroxypiperidines were also achieved under the reaction conditions similar to the lipase PS-catalyzed hydrolysis of 2a.