Cara E. Brocklehurst, Markus Furegati, J. Müller-Hartwieg
Feb 1, 2010
Citations
0
Influential Citations
4
Citations
Journal
Helvetica Chimica Acta
Abstract
α-Aminomethylation of (R)-DIOZ-alkylated (DIOZ=4-isopropyl-5,5-diphenyloxazolidin-2-one) substrates is a key step in the asymmetric synthesis of β2-amino acids, but it is unfortunately often accompanied by formation of transcarbamation by-products. Aminomethylation was tested using a range of electrophiles, and the amount of by-product formation was assessed in each case. Benzyl N-[(benzyloxy)methyl]carbamate electrophile 3d is unable to form this by-product due to its inherent benzyl substitution. Use of electrophile 3d showed an improved impurity profile in aminomethylation, thus leading to easier intermediate purification.