35648-75-0Relevant academic research and scientific papers
Nucleophilic Substitution Reactions of (Alkoxymethylene)dimethylammonium Chloride
Barrett, Anthony G. M.,Braddock, D. Christopher,James, Rachel A.,Koike, Nobuyuki,Procopiou, Panayiotis A.
, p. 6273 - 6280 (1998)
The use of imidate esters as potential replacements for diethyl azodicarboxylate and triphenylphosphine in the Mitsunobu reaction is described. A series of secondary alcohols were allowed to react with (chloromethylene)dimethylammonium chloride, generated from dimethylformamide (DMF) and oxalyl chloride, to give imidate esters. Reaction of these salts with potassium benzoate or potassium phthalimide gave the products of SN2 substitution in excellent yields with clean inversion of stereochemistry. Optimization of reaction conditions is discussed as a means to increase the atom economy of the process by minimizing the quantity of nucleophile required.
Amplification of the chiroptical response of UV-Transparent amines and alcohols by: N-phthalimide derivatization enabling absolute configuration determination through ECD computational analysis
Belviso, Sandra,Mazzeo, Giuseppe,Padula, Daniele,Santoro, Ernesto,Scafato, Patrizia,Superchi, Stefano
, p. 2094 - 2102 (2020/03/27)
The stereoselective transformation of chiral UV-Transparent amines and alcohols to phthalimides has proved to be a simple and efficient method to enhance the chiroptical response of these substrates allowing their reliable absolute configuration determination by computational analysis of ECD spectra. Such a transformation also leads to a significant reduction in the molecular conformational flexibility thus simplifying the conformational analysis required by the computational treatment. The method described herein thus allows the absolute configuration assignment to these challenging substrates to be much easier and reliable.
Nucleophilic substitution of (alkoxymethylene)dimethylammonium chloride with potassium phthalimide; a convenient procedure for the synthesis of imides with inversion of configuration
Barrett, Anthony G. M.,Braddock, D. Christopher,James, Rachel A.,Procopiou, Panayiotis A.
, p. 433 - 434 (2007/10/03)
Secondary alcohols are converted into their phthalimido derivatives with inversion of configuration via sequential reaction with (chloromethylene)dimethylammonium chloride and potassium phthalimide.
