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• 884588-09-4 7-(3,5-dinitrobenzoyl)-7-azabicyclo[4.1.0]heptane 
• 108-98-5 thiophenol 
• 4551-15-9 phenylthiotrimethylsilane 

Relevant academic research and scientific papers

Gram-scale preparation of VAPOL hydrogenphosphate: A structurally distinct chiral bronsted acid

A detailed gram-scale synthesis of VAPOL hydrogenphosphate, a structurally distinct chiral Bronsted acid, is presented. The reaction utilizes commercially available starting materials, proceeds with high yields and has been reproduced numerous times at scale. Georg Thieme Verlag Stuttgart.

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.

Guanidine-catalyzed enantioselective desymmetrization of meso-aziridines

An amino-indanol derived chiral guanidine was developed as an efficient Bronsted base catalyst for the desymmetrization of meso-aziridines with both thiols and carbamodithioic acids as nucleophiles, which provided 1,2-difunctionalized ring-opened products

Highly enantioselective synthesis of β-amidophenylthioethers by organocatalytic desymmetrization of meso- aziridines

The desymmetrization of W-acylaziridines with Me3SiSPh, catalyzed by commercially available (R) and (S)-VAPOL hydrogen phosphate, produced β-(N-acylamino)phenylthioethers in a highly enantioselective and efficient manner (78-99% ee). The select

Desymmetrization of meso-N-acylaziridines with benzenethiols promoted by α,α-Diaryl-L-prolinols

α,α-Diaryl-L-prolinols were disclosed to promote the desymmetrization of meso-N-acylaziridines with benzenethiols to afford the products in good yields and moderate enantioselectivities (up to 61% ee), which can be greatly improved to >90% ee after a sing

Chiral phosphoric acid-catalyzed desymmetrization of meso-aziridines with functionalized mercaptans

Conditions for the phosphoric acid-catalyzed highly enantioselective ring-opening of meso-aziridines with a series of functionalized aromatic thiol nucleophiles are described. The procedure utilizes commercially available aromatic thiols, a series of meso