227946-97-6Relevant academic research and scientific papers
Reversal of Regioselection in the Sharpless Asymmetric Aminohydroxylation of Aryl Ester Substrates
Morgan, Adam J.,Masse, Craig E.,Panek, James S.
, p. 1949 - 1952 (2008/02/11)
(Matrix Presented) The asymmetric synthesis of β-hydroxy-α-amino acids is reported which relies on the use of α,β-unsaturated aryl ester substrates and the dihydroquinyl alkaloid ligand system (DHQ)2-AQN to control the regio- and enantioselectivity of the asymmetric aminohydroxylation (AA) process. α,β-Unsaturated ester substrates of type 1 have a significant effect on the substrate - ligand recognition event which results in a reversal of regioselectivity in the AA reaction.
Total synthesis of (+)-lactacystin
Panek, James S.,Masse, Craig E.
, p. 1093 - 1095 (2007/10/03)
A double stereodifferentiating crotylation between aldehyde 1 and silane (S)-2 to afford homoallylic alcohol 3 is the key diastereoselective step (anti:syn > 30:1) in an efficient asymmetric synthesis of (+)-lactacystin. This compound is a metabolite isol
