New reaction conditions using trifluoroethanol for the E-I Hofmann rearrangement

Authors
Matsumura, Y Satoh, Y Shirai, K Onomura, O Maki, T
Citation
Y. Matsumura et al., New reaction conditions using trifluoroethanol for the E-I Hofmann rearrangement, J CHEM S P1, (15), 1999, pp. 2057-2060
Citations number
26
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
15
Year of publication
1999
Pages
2057 - 2060
Database
ISI
SICI code
0300-922X(19990807):15<2057:NRCUTF>2.0.ZU;2-Y
Abstract
The Hofmann rearrangement of N-2-protected glutamine esters to N-2-protecte d (2S)-4-[(2,2,2-trifluoroethoxy)carbonylamino]-2-aminobutyric acid esters was successfully achieved by an electrochemical method using a trifluoroeth anol (TFE)-MeCN solvent system where the TFE may play an important role in controlling the basicity caused by electrochemically generated bases.