31180-46-8

Upstream product

• 128-09-6 N-chloro-succinimide 
• 6651-36-1 1-(Trimethylsilyloxy)cyclohexene 
• 75-77-4 chloro-trimethyl-silane 
• 822-87-7 2-Chlorocyclohexanone 
• 16029-98-4 trimethylsilyl iodide 
• 7449-74-3 N-methyl-N-trimethylsilylacetamide 

Downstream Products

• 91873-60-8 chloro-2 (oxo-3 butyl)-2 cyclohexanone 
• 108574-33-0 chloro-2 (oxo-3 methyl-1 butyl)-2 cyclohexanone 
• 91873-61-9 chloro-2 (oxo-3 phenyl-3 propyl)-2 cyclohexanone 
• 822-87-7 2-Chlorocyclohexanone 
• 31151-37-8 (6-Chloro-cyclohex-1-enyloxy)-trimethyl-silane 

Relevant academic research and scientific papers

Silazanes/catalytic bases: Mild, powerful and chemoselective agents for the preparation of enol silyl ethers from ketones and aldehydes

We have developed an efficient method for the preparation of enol silyl ethers using novel agents, silazanes together with NaH or DBU catalyst, wherein TMS and TBDMS groups were smoothly and chemoselectively introduced into ketones and aldehydes under mil

Enantioselective protonation of silyl enol ethers and ketene disilyl acetals with Lewis acid-assisted chiral Bronsted acids: Reaction scope and mechanistic insights

Enantioselective protonation is a potent and efficient way to construct chiral carbons. Here we report details of the reaction using Lewis acid-assisted chiral Bronsted acids (chiral LBAs). The 1:1 coordinate complex of tin tetrachloride and optically active binaphthol ((R)- or (S)-BINOL) can directly protonate various silyl enol ethers and ketene disilyl acetals to give the corresponding α-aryl ketones and α-arylcarboxylic acids, respectively, with high enantiomeric excesses (up to 98% ee). A catalytic version of enantioselective protonation has also been achieved using stoichiometric amounts of 2,6-dimethylphenol and catalytic amounts of monomethyl ether of optically active BINOL in the presence of tin tetrachloride. This protonation is also effective for producing α-halocarbonyl compounds (up to 91% ee). DFT calculations on the B3LYP/LANL2DZ level show that the conformational structure of the chiral LBA and the orientation of activated proton on (R)-BINOLs are important for understanding the absolute stereochemistry of the products.

REACTIONS OF ENOL SILYL ETHERS WITH N-HALOSUCCINIMIDE - A STEPWISE PROCESS.

The N-chlorosuccinimide (NSC) reaction of a number of cyclic and acyclic trimethylsilyl enol ethers was investigated.Based on product analyses, the mechanism of the reaction is postulated to involve a step-wise process.

A CONVENIENT PREPARATION METHOD OF THE VINYLIC HALIDE ISOMER OF CHLOROTRIMETHYLSILYL ENOL ETHERS

Reaction of trimethylsilyliodide (generated in situ from trimethylsilylchloride and sodium iodide) in the presence of triethylamine in acetonitrile with α-chloroketones yields the vinylic halide isomer of chlorotrimethylsilyl enol ethers.