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Synthesis and Characterization of Intramolecularly Stabilized Chiral Dimethylindium Alkoxides and their Use as Cross Coupling Reagents
Author(s) -
Schumann Herbert,
Kaufmann Jens,
Wassermann Birgit C.,
Girgsdies Frank,
Jaber Nimer,
Blum Jochanan
Publication year - 2002
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 - 10.1002/1521-3749(200206)628:5<971::aid-zaac971>3.0.co;2-g
Subject(s) - chemistry , trimethylindium , chelation , medicinal chemistry , reagent , stereochemistry , carbon 13 nmr , polymer chemistry , organic chemistry , metalorganic vapour phase epitaxy , epitaxy , layer (electronics)
The enantiomerically pure dimeric N, O‐5‐chelates [Me 2 In(μ‐OCH 2 CH(R)NMe 2 )] 2 {R = Me ( S ) ( 2 ); R = i Pr ( S ) ( 3 ); R = i Bu ( S ) ( 4 ); R = Bz ( S ) ( 5 )}, and [Me 2 In‐{μ‐(1 R , 2 S )‐OCH(Ph)CH(Me)NMe 2 }] 2 ( 6 ), as well as the achiral dimeric N, O‐6‐chelate [Me 2 In(μ‐O(CH 2 ) 3 NMe 2 )] 2 ( 7 ) have been synthesized from trimethylindium and equimolar amounts of the corresponding enantiomerically pure dimethylamino alcohols or of the achiral dimethylaminopropanol by elimination of methane. Their 1 H NMR, 13 C NMR, and mass spectra as well as the X‐ray single crystal structure analyses of [Me 2 In{μ‐O(CH 2 ) 2 NMe 2 }] 2 ( 1 ), 3, 5, 6 and 7 are described and discussed. The coordinative N→In bonds of the five‐coordinate indium complexes show dynamic dissociation/association processes. 1—6 were found to be useful reagents for the partial kinetic resolution of 2‐carbomethoxy‐1, 1′‐binaphthyl triflate.