111060-91-4Relevant academic research and scientific papers
Stereoselective Arylation of Amino Aldehydes: Overriding Natural Substrate Control through Chelation
Martins, Bruna S.,Moro, Angélica V.,Lüdtke, Diogo S.
, p. 3334 - 3340 (2017)
The chelation-controlled arylation reaction of chiral, enantiopure acyclic α-amino aldehydes enabled by a B/Zn exchange reaction between arylboronic acids and Et2Zn is reported. The presence of dibenzyl substituents at the nitrogen plays a key role in the stereochemical outcome of the reaction, and chelation is favored over the natural tendency of this type of substrate to undergo Felkin-Anh controlled additions with organomagnesium and organolithium reagents.
NON-RACEMIZING SYNTHESIS AND STEREOSELECTIVE REDUCTION OF CHIRAL α-AMINO KETONES
Reetz, M. T.,Drewes, M. W.,Lennick, K.,Schmitz, A.,Holdgruen, X.
, p. 375 - 378 (2007/10/02)
α-Amino acids can be doubly benzylated at nitrogen, forming N,N-dibenzyl amino acids which can be converted into α-amino ketones 4 without appreciable racemization.The latter undergo stereoselective reduction with NaBH4 under non-chelation control to form
