jo026622f_si_001.pdf (518.12 kB)
Facile N-Derivatization of α-Amino Esters and Amides via Benzotriazolylmethyl Derivatives
journal contribution
posted on 2003-10-23, 00:00 authored by Alan R. Katritzky, Nataliya Kirichenko, Boris V. Rogovoy, Hai-Ying Heα-(N-Substituted amino)esters were prepared in a two-step procedure from available unsubstituted
α-amino esters. α-Amino esters are first converted into the corresponding N-benzotriazolylmethyl
derivatives; in the second step, the benzotriazole group is substituted by various nucleophiles with
or without the presence of a Lewis acid to give substituted α-amino esters in high overall yield
under mild conditions with no signs of racemization. Boc-protected amino acids were converted
into α-amino amides; subsequent deprotection allowed the conversion into N-substituted derivatives
analogously to the α-amino esters, without racemization in high yields under mild conditions.
History
Usage metrics
Categories
- Biochemistry
- Medicine
- Genetics
- Molecular Biology
- Neuroscience
- Physiology
- Evolutionary Biology
- Environmental Sciences not elsewhere classified
- Chemical Sciences not elsewhere classified
- Ecology
- Astronomical and Space Sciences not elsewhere classified
- Immunology
- Developmental Biology
- Plant Biology
- Virology
- Computational Biology
Licence
Exports
RefWorks
BibTeX
Ref. manager
Endnote
DataCite
NLM
DC