1334292-75-9Relevant academic research and scientific papers
Overcoming product inhibition in catalysis of the intramolecular Schmidt reaction
Motiwala, Hashim F.,Fehl, Charlie,Li, Sze-Wan,Hirt, Erin,Porubsky, Patrick,Aube, Jeffrey
, p. 9000 - 9009 (2013/07/26)
A method for carrying out the intramolecular Schmidt reaction of alkyl azides and ketones using a substoichiometric amount of catalyst is reported. Following extensive screening, the use of the strong hydrogen-bond-donating solvent hexafluoro-2-propanol was found to be consistent with low catalyst loadings, which ranged from 2.5 mol % for favorable substrates to 25 mol % for more difficult cases. Reaction optimization, broad substrate scope, and preliminary mechanistic studies of this improved version of the reaction are described.
In situ generation and intramolecular schmidt reaction of keto azides in a microwave-assisted flow format
Painter, Thomas O.,Thornton, Paul D.,Orestano, Mario,Santini, Conrad,Organ, Michael G.,Aube, Jeffrey
, p. 9595 - 9598 (2011/10/04)
Go with the flow! A method for conversion of keto halides to lactams by means of sequential azidation and intramolecular Schmidt reaction in a combined flow format is described (see scheme; MWI=microwave irradiation, TFA=trifluoroacetic acid).
