188300-52-9

Upstream product

• 102-92-1 cinnamoyl chloride 
• 34837-55-3 Phenylselenyl bromide 
• 147-85-3 L-proline 
• 188300-62-1 (S)-1-[(E)-(3-Phenyl-acryloyl)]-pyrrolidine-2-carboxylic acid amide 
• 102-92-1 Cinnamoyl chloride 
• 107173-65-9 N-(3-phenylpropenoyl)-L-proline 
• 188300-51-8 (3R,4R,9aS)-3-Phenyl-4-phenylselanyl-hexahydro-pyrrolo[1,2-a][1,4]diazepine-1,5-dione 

Downstream Products

• 188300-53-0 (S)-3-Phenyl-7,8,9,9a-tetrahydro-2H-pyrrolo[1,2-a][1,4]diazepine-1,5-dione 

Relevant academic research and scientific papers

Novel asymmetric phenylselenium-induced lactamizations of olefinic amides: Stereoselective routes to α- and β-amino acids

Organoselenium-induced cyclofunctionalization of the (S)-N-(α,β-unsaturated) acylprolinamides 1, 7 and 14 has been found to produce the 7-membered bislactam products 2 and 15, or the 6-membered phenylselenolactam products 8 and 9 depending on the substitution pattern of the enone moiety of the starting material. The structural identities and stereochemistry of the cyclized products have been determined by X-ray diffraction, and the diastereoselectivity in the formation of the 7-membered ring bislactam product was found to be 91.6% de. The mechanism of the cyclolactamization is discussed.

A diastereoselective phenylselenium-induced lactamization of olefimic amides. A possible route to α- and β-amino acid derivatives

The organoselenium-induced cyclofunctionalization of (S)-N-(α,β-unsaturated-acyl)prolinamides was found to produce with a high degree of chirality transfer, 7- and 6-membered bislactam derivatives depending on the substitution pattern of the starting material.