Unprecedented migration of N-alkoxycarbonyl groups in protected pyroglutaminol

Authors
Bunch, L Norrby, PO Frydenvang, K Krogsgaard-Larsen, P Madsen, U
Citation
L. Bunch et al., Unprecedented migration of N-alkoxycarbonyl groups in protected pyroglutaminol, ORG LETT, 3(3), 2001, pp. 433-435
Citations number
11
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
3
Year of publication
2001
Pages
433 - 435
Database
ISI
SICI code
1523-7060(20010208)3:3<433:UMONGI>2.0.ZU;2-Z
Abstract
[GRAPHICS] Cleavage of an O-silyl ether in an NBOC protected pyroglutaminol using TBAF led to an unprecedented migration of the BOC group. An investigation of th e mechanism, based on experimental data and quantum mechanical calculations , is presented. Similar migration was observed for KCbz and N-methoxycarbon yl groups.