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1‐Aminoindan‐2‐ol, a Suitable Ligand for the Synthesis of Chiral, Intramolecularly Stabilized Compounds of Aluminum, Gallium, and Indium
Author(s) -
Schumann Herbert,
Kaufmann Jens,
Dechert Sebastian
Publication year - 2004
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.200400236
Subject(s) - chemistry , indium , gallium , stereochemistry , metal , nuclear magnetic resonance spectroscopy , medicinal chemistry , proton nmr , crystallography , organic chemistry
The reactions of enantiomerically pure (1 R , 2 S )‐(+)‐ cis ‐1‐aminoindan‐2‐ol, (1 S , 2 R )‐(‐)‐ cis ‐1‐aminoindan‐2‐ol, and racemic trans ‐1‐aminoindan‐2‐ol with trimethylaluminum, ‐gallium, and ‐indium produce the intramolecularly stabilized, enantiomerically pure dimethylmetal‐1‐amino‐2‐indanolates (1 R , 2 S )‐(+)‐ cis ‐Me 2 AlO‐2‐C*HC 7 H 6 ‐1‐C*HNH 2 ( 1 ), (1 S , 2 R )‐(‐)‐ cis ‐Me 2 AlO‐2C*HC 7 H 6 ‐1‐C*HNH 2 ( 2 ), (1 R , 2 S )‐(+)‐ cis ‐Me 2 GaO‐2‐C*HC 7 H 6 ‐1‐C*HNH 2 ( 3 ), (1 R , 2 S )‐(+)‐ cis ‐Me 2 InO‐2‐C*HC 7 H 6 ‐1‐C*HNH 2 ( 4 ), (1 S , 2 R )‐(‐)‐ cis ‐Me 2 InO‐2‐C*HC 7 H 6 ‐1‐C*HNH 2 ( 5 ), and racemic (+/‐)‐ trans ‐Me 2 InO‐2‐C*HC 7 H 6 ‐1‐C*HNH 2 ( 6 ). The compounds were characterized by 1 H NMR, 13 C NMR, 27 Al NMR and mass spectra as well as 1 and 3 to 6 by determination of their crystal and molecular structures. The dynamic dissociation/association behavior of the coordinative metal‐nitrogen bond was studied by low temperature 1 H NMR spectroscopy.