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Resolution of seven-coordinate complexes.

Journal article
Authors Anders Lennartson
Marcus Vestergren
Mikael Håkansson
Published in Chemistry (Weinheim an der Bergstrasse, Germany)
Volume 11
Issue 6
Pages 1757-62
ISSN 0947-6539
Publication year 2005
Published at Department of Chemistry
Pages 1757-62
Language en
Links dx.doi.org/10.1002/chem.200401019
Subject categories Organic Chemistry

Abstract

The crystal structures of [Pr(dbm)3H2O] (1), [Sm(dbm)3H2O] (2), and [Er(dbm)3H2O] (3) have been determined (dbm=dibenzoylmethane). They display seven-coordinate propeller-shaped molecules, which are chiral and crystallize as conglomerates in space group R3. Analysis of the crystal structures reveals supramolecular interactions, including formation of a quadruple helix, which explain how stereochemical information can be transferred between stacks of molecules. A method to quantify the ee in bulk samples of stereochemically labile compounds by using solid-state CD spectroscopy is described. Using this method, it has been shown that compounds 1-3 undergo total spontaneous resolution directly after synthesis, forming a microcrystalline reaction product that is essentially enantiopure. The resolution of bulk quantities of seven-coordinate complexes (without chiral or polydentate ligands) is thus reported for the first time. Because the crystallization starts without seeding, the overall preparation may be regarded as absolute asymmetric synthesis.

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