P[(S,S,S)-PhHMeCNCH2CH2](3)N: A new chiral P-31 and H-1 NMR spectroscopic reagent for the direct determination of ee values of chiral azides

Authors
Liu, XD Ilankumaran, P Guzei, IA Verkade, JG
Citation
Xd. Liu et al., P[(S,S,S)-PhHMeCNCH2CH2](3)N: A new chiral P-31 and H-1 NMR spectroscopic reagent for the direct determination of ee values of chiral azides, J ORG CHEM, 65(3), 2000, pp. 701-706
Citations number
44
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF ORGANIC CHEMISTRY
ISSN journal
00223263 → ACNP
Volume
65
Issue
3
Year of publication
2000
Pages
701 - 706
Database
ISI
SICI code
0022-3263(20000211)65:3<701:PANCPA>2.0.ZU;2-W
Abstract
A facile and economical procedure for the synthesis of the C-3 chiral alpha -phenylethylamino trisaminoamine [(S,S,S)-PhHMeCNHCH2CH2](3)N in good yield is reported. The corresponding bicyclic proazaphosphatrane P[(S,S,S)-PhHMe CNCH2CH2](3)N, its bicydic phosphoryl derivative, and its tricyclic P-proto nated azaphosphatrane were also synthesized and characterized. It is found that the proazaphosphatrane is an efficient derivatizing agent for the dire ct determination of enantiomeric ratios of chiral azides by means of (31)p and H-1 NMR spectroscopy.