Malkov, A. V., Vrankova, K., Cerny, M. and Kocovsky, P. (2009) On the Selective N-Methylation of BOC-Protected Amino Acids. Journal of Organic Chemistry, 74(21), pp. 8425-8427. (doi: 10.1021/jo9016293)
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Abstract
The selective N-methylation of BOC-protected valine 1a with MeI and NaH in THF (i.e, in the presence of it free carboxyl group) has been attributed to the protection of the carboxylate by chelation to Na+. An alternative mechanism, involving the Formation of the carbene intermediate generated from MeI and its Insertion Into the N-H bond, has been ruled out by isotopic labeling.
| Item Type: | Articles |
|---|---|
| Keywords: | ACID ACIDS Amino acids AMINO-ACIDS AROMATIC KETIMINES Asymmetric reduction BOND DERIVATIVES ENANTIOMERIC PURITY Enantioselective reduction IMINES MECHANISM METHYLAMINO ACIDS PEPTIDE-SYNTHESIS POLYMER-SUPPORTED ORGANOCATALYSTS Trichlorosilane |
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Malkov, Dr Andrei and Kocovsky, Professor Pavel |
| Authors: | Malkov, A. V., Vrankova, K., Cerny, M., and Kocovsky, P. |
| College/School: | College of Science and Engineering > School of Chemistry |
| Journal Name: | Journal of Organic Chemistry |
| ISSN: | 0022-3263 |
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