1415893-18-3

Upstream product

• 645-96-5 Benzeneselenol 
• 72726-46-6 tert-butyl(dimethyl)(phenylseleno)silane 
• 884588-09-4 7-(3,5-dinitrobenzoyl)-7-azabicyclo[4.1.0]heptane 
• 33861-17-5 phenyl trimethylsilyl selenide 

Downstream Products

• 1334404-90-8 C₁₃H₁₃N₃O₅ 

Relevant academic research and scientific papers

Studies on the true catalyst in the phosphate-promoted desymmetrization of meso-aziridines with silylated nucleophiles

Significant amounts of metal phosphate impurities have been detected by NMR spectroscopy and ICP-OES analysis of synthetic, as well as purchased, samples of VAPOL hydrogen phosphate purified on silica gel. The previously reported VAPOL hydrogen phosphate-catalyzed desymmetrization of meso-aziridines with different silylated compounds, has been re-examined. While metal-free phosphoric acid exhibited low activity and enantioselectivity, calcium and magnesium phosphate salts proved to be the true catalysts in these related processes. Reproducible high enantioselectivities were obtained in the ring-opening of cyclic meso-aziridines with Me3SiX (X=SPh, SePh, N3) employing a 1:1 mixture of calcium and magnesium VAPOL phosphates. The reaction has been successfully extended to Me3SiSBn, Me3SiSMe and Me3SiNCS, giving ring-opened products in high yield and unprecedented moderate to good enantioselectivities.

A general phosphoric acid-catalyzed desymmetrization of meso-aziridines with silylated selenium nucleophiles

The first example of meso-aziridine desymmetrization with selenium nucleophiles is reported. The reaction, promoted by VAPOL-hydrogen phosphate using (phenylseleno)trimethylsilane as the nucleophile, proves to be very general and highly enantioselective (84-99% ee).