182161-97-3Relevant academic research and scientific papers
Chirally templated boronic acid Mannich reaction in the synthesis of optically active α-amino acids
Currie, Gordon S.,Drew, Michael G.B.,Harwood, Laurence M.,Hughes, David J.,Luke, Richard W.A.,Vickers, Richard J.
, p. 2982 - 2990 (2007/10/03)
Adducts from diastereoselective Mannich-type reactions of aldehydes, 2-furylboronic acid and the chiral amine template (S)-5-phenylmorpholin-2-one, were used in the synthesis of a series of enantiomerically pure D-α-amino acids. The direction of diastereocontrol was proved by X-ray crystallography analysis of the reaction products. Results indicated that sequential degradation of diastereomically pure N-furfurylmorpholinones obtained by boronic Mannich condensation, could be carried out to produce amino acids of high optical purity.
Asymmetry in the boronic acid Mannich reaction: Diastereocontrolled addition to chiral iminium species derived from aldehydes and (S)-5-phenylmorpholin-2-one
Harwood, Laurence M.,Currie, Gordon S.,Drew, Michael G. B.,Luke, Richard W. A.
, p. 1953 - 1954 (2007/10/03)
(S)-5-Phenylmorpholin-2-one? and a range of aliphatic aldehydes form chiral iminium intermediates which undergo diastereoselective Mannich reactions with 2-furylboronic acid. Single crystal X-ray analysis of methylated derivative 4 derived from major adduct 2g confirms the stereochemical course of the reaction.
