Rationalization of the stereochemistry of an addition of dialkyl phosphites to certain chiral aldimines: The experimental and theoretical approach

✍ Scribed by Ryszard B. Nazarski; Jarosław A. Lewkowski; Romuald Skowroński

• Publisher: John Wiley and Sons
• Year: 2002
• Tongue: English
• Weight: 150 KB
• Volume: 13
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.10005

✦ Synopsis

Abstract

The absolute configuration of an α‐P stereogenic center in two diastereomeric O,O‐dialkyl α‐aminophosphonates (3), arising from an induced 1,3‐asymmetric phosphite addition to the CN bond of furfural‐derived Schiff bases (1), was established from single product ^1^H NMR data. Such spectra were interpreted with anisotropic shielding in relation to the AM1 and MNDO/d structures of 3; the former ones turned out to be closer to the obtained experimental results (^1^H NMR spectra of 3, crystallographic database study). Since favored 3‐21G geometries of starting imines 1 were modeled as well, it was inferred that a stereochemical outcome of this reaction is governed by Cram selectivity. © 2002 Wiley Periodicals, Inc. Heteroatom Chem 13:120–125, 2002; Published online in Wiley Interscience (www.interscience.wiley.com). DOI 10.1002/hc.10005