BenzylN-[(Benzyloxy)methyl]carbamate: An Improved Aminomethylation Electrophile for the Synthesis of (Benzyloxy)carbonyl (Cbz)-Protected Chiralβ2-Amino Acids
| Autor: | Markus Furegati, Cara E. Brocklehurst, Flavio Ossola, Luigi La Vecchia, J. Constanze D. Müller-Hartwieg |
|---|---|
| Rok vydání: | 2010 |
| Předmět: |
chemistry.chemical_classification
Carbamate medicine.medical_treatment Organic Chemistry Enantioselective synthesis Biochemistry Medicinal chemistry Catalysis Methyl carbamate Amino acid Inorganic Chemistry chemistry.chemical_compound chemistry Drug Discovery Electrophile medicine Organic chemistry Physical and Theoretical Chemistry |
| Zdroj: | Helvetica Chimica Acta. 93:314-323 |
| ISSN: | 1522-2675 0018-019X |
| DOI: | 10.1002/hlca.200900401 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Plný text