102774-93-6Relevant articles and documents
Synthesis of enantiopure cyclopropyl esters from (-)-levoglucosenone
Stockton, Kieran P.,Greatrex, Ben W.
, p. 7520 - 7528 (2016/08/16)
The biorenewable chiral synthon (-)-levoglucosenone has been converted to enantiopure cyclopropyl esters using the base-promoted carbocyclisation of 4,5-epoxyvalerates. This protocol was applied to the enantiospecific synthesis of the GABAc receptor agonist (1R,2R)-trans-2-aminomethylcyclopropanecarboxylic acid ((-)-TAMP) and its enantiomer. The process was also extended to generate 1,1,2- and 1,2,3-trisubstituted cyclopropanes resulting in a formal synthesis of the selective glutamate receptor antagonist PCCG-4.
Concise Enantioselective Synthesis of Naturally Active (S)-3-Hydroxypiperidine
Dey, Soumen,Karabal, Pratibha U.,Sudalai, Arumugam
supporting information, p. 1559 - 1565 (2015/06/02)
A short and efficient enantioselective synthesis of natural product (S)-3-hydroxypiperidine has been achieved starting from commercially available raw materials employing two catalytic routes: (i) cocatalyzed hydrolytic kinetic resolution (HKR) of racemic methyl-3-(oxiran-2-yl)propanoate; (ii) proline-catalyzed α-aminooxylation followed by Horner-Wardsworth-Emmons olefination in high enantiomeric purity (97% ee) and high overall yield (38%). (Chemical Equation Presented).
