o-Phthalaldehyde catalyzed hydrolysis of organophosphinic amides and other P(=O)-NH containing compounds

• Published in: Chemical communications (Cambridge, England) Vol. 53; no. 62; pp. 8667 - 8670
• Main Authors: Li, Bin-Jie, Simard, Ryan D., Beauchemin, Andre M.
• Format: Journal Article
• Language: English
• Published: CAMBRIDGE Royal Soc Chemistry 11.08.2017
• Subjects: Chemistry; Chemistry, Multidisciplinary; Physical Sciences; Science & Technology; P-N BOND; ASYMMETRIC-SYNTHESIS; C-H ARYLATION; ENANTIOSELECTIVE SYNTHESIS; HYDROXYL-DIRECTED METHANOLYSIS; PHOSPHORAMIDIC ACID; ALPHA-AMINO-ACIDS; ENAMINE CATALYSIS; ASSISTED HYDROLYSIS; INDUCED INTRAMOLECULARITY

Over 50 years ago, Jencks and Gilchrist showed that formaldehyde catalyses the hydrolysis of phosphoramidate through electrophilic activation, induced by covalent attachment to its nitrogen atom. Given our interest in the use of aldehydes as catalysts, this work was revisited to identify a superior...