Benzyl N ‐[(Benzyloxy)methyl]carbamate: An Improved Aminomethylation Electrophile for the Synthesis of (Benzyloxy)carbonyl (Cbz)‐Protected Chiral β 2 ‐Amino Acids

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 β 2 ‐amino acids, but it is unfortunately often accompanied by formation of transcarbamation by‐products. Aminomethylation was tested using a r...

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Published inHelvetica chimica acta Vol. 93; no. 2; pp. 314 - 323
Main Authors Brocklehurst, Cara E., Furegati, Markus, Müller‐Hartwieg, J. Constanze D., Ossola, Flavio, La Vecchia, Luigi
Format Journal Article
LanguageEnglish
Published 01.02.2010
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Summary: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 β 2 ‐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.
ISSN:0018-019X
1522-2675
DOI:10.1002/hlca.200900401