Diastereoselective self-assembly of chiral diamine-chelated aryllithiums to dimeric aggregates.
Aryllithium compounds [LiC6H4(CH2N(Et)CH2CH2NEt2)-2]2 (2b), [LiC6H4(CH(Me)N(Me)CH2CH2NMe2-(R))-2]2 ((R)-3b), and [LiC6H4(CH(Me)N(Me)CH2CH2NMe2-(rac))-2]2 ((rac)-3b) were synthesized and characterized in the solid state and in solution. X-ray crystallographic studies of 2b and (R)-3b and molecular weight determinations of 2b, (R)-3b, and (rac)-3b by cryoscopy in benzene showed that, both in the solid state and in apolar, noncoordinating solvents such as benzene, these compounds exist as discrete dimeric aggregates. For (R)-3b and (rac)-3b the aggregation process of two monomeric aryllithium units to one dimer is highly diastereoselective.
Arink
Anne M
AM
Debye Institute, Department of Metal-Mediated Synthesis, Utrecht University, Padualaan 8, 3584 CH Utrecht, The Netherlands.
Kronenburg
Claudia M P
CM
Jastrzebski
Johann T B H
JT
Lutz
Martin
M
Spek
Anthony L
AL
Gossage
Robert A
RA
van Koten
Gerard
G