245123-65-3Relevant academic research and scientific papers
Chiral ion-pair organocatalyst promotes highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols
Shen, Zhigao,Pan, Xixian,Lai, Yisheng,Hu, Jiadong,Wan, Xiaolong,Li, Xiaoge,Zhang, Hui,Xie, Weiqing
, p. 6986 - 6990 (2015)
By designing a novel chiral ion-pair organocatalyst composed of chiral phosphate and DABCO-derived quaternary ammonium, highly enantioselective 3-exo iodo-cycloetherification of allyl alcohols was achieved using NIS as a halogen source. Based on this reaction, one-pot asymmetric 3-exo iodo-cycloetherification/Wagner-Meerwein rearrangement of allyl alcohols en route to enantioenriched 2-iodomethyl-2-aryl cycloalkanones was subsequently developed. Due to the participation of adjacent iodine, the Wagner-Meerwein rearrangement of 2-iodomethyl-2-aryl epoxide proceeds with unusual retention of stereoconfiguration.
PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE HYDROXYMETHYLATED COMPOUNDS
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Page/Page column 6, (2010/11/24)
The present invention presents a catalyst that allows asymmetric hydroxymethylation reactions to progress with excellent asymmetric selectivity and a production method for optically active hydroxymethylated compounds using the catalyst. Optically active h
Lewis acid-activated chiral leaving group: Enantioselective electrophilic addition to prochiral olefins
Nakamura, Hiroko,Ishihara, Kazuaki,Yamamoto, Hisashi
, p. 5124 - 5137 (2007/10/03)
A new strategy using a BINOL derivative as a chiral leaving group and Lewis acid has been developed for enantioselective alkylation of prochiral olefins. (R)-2,2′-Bis[2-(trimethylsilyl)ethoxy- methyl]-1,1′-binaphthol is demonstrated to be an effective reagent for enantioselective hydroxymethylation of silyl enol ethers and trisubstituted alkenes. Electrophilic addition to prochiral olefins is accompanied by cleavage of an acetal that is dual activated by SnCl4 and the δ-effect of silicon through the SN2 substitution process. Enantioselective synthesis of cyclic terpenes is also described using this strategy.
