464157-77-5Relevant academic research and scientific papers
Direct organo-catalytic asymmetric α-amination of aldehydes - A simple approach to optically active α-amino aldehydes, α-amino alcohols, and α-amino acids
Bogevig, Anders,Juhl, Karsten,Kumaragurubaran, Nagaswamy,Zhuang, Wei,Jorgensen, Karl Anker
, p. 1790 - 1793 (2002)
L-Proline as the catalyst: The first direct asymmetric α-amination of aldehydes using L-proline as the catalyst is presented (see scheme; Pg = protecting group). This new reaction gives easy access to optically active α-amino aldehydes, α-amino alcohols, and α-amino acids from simple and easily available starting materials and catalysts. The reactions proceed in high yields and excellent enantioselectivities with as little as 2 mol % of the catalyst.
A Designed Approach to Enantiodivergent Enamine Catalysis
Macharia, Juliet,Wambua, Victor,Hong, Yun,Harris, Lawrence,Hirschi, Jennifer S.,Evans, Gary B.,Vetticatt, Mathew J.
supporting information, p. 8756 - 8760 (2017/07/17)
The rational design and implementation of enantiodivergent enamine catalysis is reported. A simple secondary amine catalyst, 2-methyl-l-proline, and its tetrabutylammonium salt function as an enantiodivergent catalyst pair delivering the enantiomers of α-functionalized aldehyde products in excellent enantioselectivities. This novel concept of designed enantiodivergence is applied to the enantioselective α-amination, aldol, and α-aminoxylation/α-hydroxyamination reactions of aldehydes.
Chemoselective room temperature E1cB N-N cleavage of oxazolidinone hydrazides from enantioselective aldehyde α-hydrazination: Synthesis of (+)-1,4-dideoxyallonojirimycin
Ferreira, Jasmin,Rees-Jones, Sophie C. M.,Ramaotsoa, Valerie,Msutu, Ath'enkosi,Hunter, Roger
, p. 1545 - 1549 (2016/02/09)
Room temperature E1cB N-N cleavage of oxazolidinone hydrazides via N-alkylation with diethyl bromomalonate and potassium or caesium carbonate as base in acetonitrile is presented. The new method has a much improved chemoselectivity, which is illustrated by a concise total synthesis of the piperidine iminosugar (+)-1,4-dideoxyallonojirimycin.
