68758-68-9Relevant articles and documents
Generation and conjugate additions of o-quinone methides under mild base conditions: Rapid synthesis of n-substituted aryl glycine derivatives
Wang, Wei,Zheng, Zhong,Wang, Xiangmin,Chen, Jinchun
, p. 8299 - 8306 (2014/01/06)
A one-step approach was observed to give N-substituted aryl glycine derivatives in good to excellent yields (up to 93 %) from (ortho-hydroxymethyl) aryl benzoates. A cascade mechanism was proposed for the generation and in situ conjugate addition of the ortho-quinone methides. This mechanism is strongly supported by our subsequent findings that tertiary amines could promote the process. Different functional groups on the (ortho-hydroxymethyl)aryl benzoates and various amines were investigated to explore the scope of this cascade process. The substituents on the substrates strongly affected the reaction time and yield, and various primary and secondary amines were used as nucleophiles. The addition of tertiary amines enhanced the addition process for less basic nucleophiles. A one-step cascade approach was observed to give N-substituted aryl glycine derivatives from (ortho-hydroxymethyl)aryl benzoates under very mild conditions. The proposed mechanism involves the generation of an ortho-quinone methide and its in situ conjugate addition. Various substituent groups on the substrate and different amines as the nucleophile were investigated. Copyright
Reduction of activated carbonyl groups by alkyl phosphines: Formation of α-hydroxy esters and ketones
Zhang, Wen,Shi, Min
, p. 1218 - 1220 (2008/02/03)
Reduction of activated carbonyl groups such as α-keto esters, benzils, 1,2-cyclohexanedione, and α-ketophosphonates by alkyl phosphines afforded the corresponding α-hydroxy esters or ketones in good to excellent yields in THF at room temperature. The mechanism of the proton transfer and intramolecular hydrolysis has been studied on the basis of deuterium and 18O labeling experiments. The Royal Society of Chemistry 2006.
