69805-63-6Relevant academic research and scientific papers
Unlocking the Accessibility of Alkyl Radicals from Boronic Acids through Solvent-Assisted Organophotoredox Activation
Ranjan, Prabhat,Pillitteri, Serena,Coppola, Guglielmo,Oliva, Monica,Van der Eycken, Erik V.,Sharma, Upendra K.
, p. 10862 - 10870 (2021/09/08)
Despite their prevalence in organic synthesis, the application of boronic acids (BAs) as alkyl radical precursors in visible-light-assisted photocatalyzed reactions has been limited by their high oxidation potential. This study demonstrates the prominent
Cu(OTf)2-Promoted 1,4-addition of alkyl bromides to dehydroalanine
Shin, Jung-Ah,Kim, Jiheon,Lee, Hongsoo,Ha, Sura,Lee, Hee-Yoon
, p. 4558 - 4565 (2019/05/01)
Zn/Cu(OTf)2-mediated addition of alkyl bromides to dehydroalanine (Dha) derivatives including dipeptides and tripeptides in good to high yields under an aqueous medium was developed. This protocol allows selective and biocompatible access to various amino acid units from Dha derivatives.
One-pot synthesis of α-amino acids from CO2 using a bismetal reagent with Si-B bond
Mita, Tsuyoshi,Chen, Jianyang,Sugawara, Masumi,Sato, Yoshihiro
, p. 6202 - 6205 (2013/02/23)
In the presence of 1.1 equiv of PhMe2Si-Bpin, 5 equiv of CsF, and 20 mol % of TsOH·H2O, precursors of N-Boc-imines can be converted into the corresponding α-aryl or α-alkenyl glycine derivatives under gaseous CO2 in moderate-to-high yields with a single operation. α-Isobutenyl glycine thus obtained can be further derivatized into various types of α-amino acids including N-Boc-leucine, serine, and glycine derivatives in short steps.
Enantiomeric resolution of α-amino acid derivatives on two diastereomeric chiral stationary phases based on chiral crown ethers incorporating two different chiral units
Kim, Hee Jin,Choi, Hee Jung,Cho, Yoon Jae,Hyun, Myung Ho
body text, p. 1551 - 1554 (2010/10/20)
Two diastereomeric chiral stationary phases (CSPs) were applied to the liquid chromatographic resolution of various racemic a-amino methyl esters, α-amino N,N-diethylamides and α-amino N-propylamides. The CSP incorporating (R)-3,3' -diphenyl-1,1' -binaphtyl and (R,R)-tartaric acid unit as chiral barriers did not show any chiral recognition. In contrast, the CSP incorporating (R)-3,3'-diphenyl-1,1'-binaphtyl and (S,S)-tartaric acid unit as chiral barriers was found to show excellent chiral recognition especially for the two enantiomers of a-amino N-propylamides. Some of a-amino methyl esters and α-amino N,N-diethylamides were also resolved on the CSP incorporating (R)-3,3'-diphenyl-1,1'-binaphtyl and (S,S)-tartaric acid unit. From these results it was concluded that the two chiral units composing the diastereomeric CSPs can show "matched" or "mismatched" effect on the chiral recognition according to their absolute stereochemistry.
Stereoselective reduction of N-hydroxy-α-iminocarbonyl-oligopeptide methyl esters with Zn-MsOH
Kise, Naoki,Takaoka, Shuji,Yamauchi, Masahiro,Ueda, Nasuo
, p. 7297 - 7300 (2007/10/03)
The reduction of N-hydroxy-α-imino esters with Zn-MsOH in THF afforded α-amino esters in high yields. The reduction of N-hydroxy-α-iminocarbonyl-oligopeptide methyl esters prepared from L-phenylalanine and L-leucine di-, tri-, tetrapeptides gave the corre
Electrophilic amination of racemic and non-racemic allenyltitaniums. One-pot synthesis of α-hydrazinoalkynes from propargylic alcohol derivatives
An, Duk Keun,Hirakawa, Koichiro,Okamoto, Sentaro,Sato, Fumie
, p. 3737 - 3740 (2007/10/03)
Successive treatment of propargylic carbonates or phosphates with a Ti(O-i-Pr)4/2i-PrMgCl reagent and dialkyl azodicarboxylates gave α- hydrazinoalkynes in good yields. The reaction, which proceeded with up to 86% chiral transfer, thus has opened up a new route to optically active α- hydrazinoalkynes from the optically active propargylic compounds.
