A simple circular dichroism method for the determination of the absolute configuration of allylic amines

Citation
P. Skowronek et J. Gawronski, A simple circular dichroism method for the determination of the absolute configuration of allylic amines, TETRAHEDR L, 41(16), 2000, pp. 2975-2977
Citations number
17
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
41
Issue
16
Year of publication
2000
Pages
2975 - 2977
Database
ISI
SICI code
0040-4039(20000415)41:16<2975:ASCDMF>2.0.ZU;2-A
Abstract
Absolute configurations of C(alpha)-chiral primary allylic amines can be de termined from the CD spectra of their N-phthaloyl derivatives. This method is based on the exciton coupling of the allowed -pi-pi* transitions in the phthalimide and olefin chromophores: positive helicity of the N-C-alpha-C=C bond system results in a positive Cotton effect at ca. 220 nm, a negative Cotton effect is obtained for the negative helicity N-C-alpha-C=C bond chai n. (C) 2000 Elsevier Science Ltd. All rights reserved.