A novel traceless resin-bound guanidinylating reagent for secondary aminesto prepare N,N-disubstituted guanidines

Citation
Cw. Zapf et al., A novel traceless resin-bound guanidinylating reagent for secondary aminesto prepare N,N-disubstituted guanidines, ORG LETT, 3(8), 2001, pp. 1133-1136
Citations number
30
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
8
Year of publication
2001
Pages
1133 - 1136
Database
ISI
SICI code
1523-7060(20010419)3:8<1133:ANTRGR>2.0.ZU;2-M
Abstract
We report the development of a solid support linked guanidinylating reagent . This reagent consists of a urethane-protected triflyl guanidine attached to the resin via a carbamate linker. It allows for rapid synthesis of guani dines from a variety of amines, It provides access to N-alkyl/aryl- or N,N- dialkylguanidines under mild conditions. Cleavage with 50% TFA produces tar get molecules in high yields and purity. The ability to guanidinylate secon dary amines is a significant feature of this guanidinylating reagent.