A Stereospecific, Intermolecular Biaryl-Coupling Approach to Korupensamine A En Route to the Michellamines.
By what means and how well can axial chirality be controlled in an intermolecular Suzuki biaryl cross-coupling reaction? The directionality of reductive elimination [Eq. (1)] is completely controlled by using a strategically positioned internal ligand L to afford a single biaryl atropisomer corresponding to the korupensamine A skeleton. TIPS=iPr(3)Si, Ts=H(3)CC(6)H(4)SO(2).
Lipshutz
BH
Department of Chemistry, University of California, Santa Barbara, CA 93106 (USA).
Keith
JM