Using polarization effects to alter chemical reactivity: A simple host which enhances amine nucleophilicity

Authors
Ashton, PR Calcagno, P Spencer, N Harris, KDM Philp, D
Citation
Pr. Ashton et al., Using polarization effects to alter chemical reactivity: A simple host which enhances amine nucleophilicity, ORG LETT, 2(10), 2000, pp. 1365-1368
Citations number
23
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
10
Year of publication
2000
Pages
1365 - 1368
Database
ISI
SICI code
1523-7060(20000518)2:10<1365:UPETAC>2.0.ZU;2-P
Abstract
The rational design of a bis(phosphine oxide) host which is capable of bind ing a benzylic amine is presented. The ability of this host to increase the rate of addition of 4-fluorobenzylamine to N-phenylmaleimide is rationaliz ed in terms of the enhancement of the nucleophilicity of the benzylic amine .