A Stereospecific, Intermolecular Biaryl-Coupling Approach to Korupensamine A En Route to the Michellamines

Angew Chem Int Ed Engl. 1999 Dec 3;38(23):3530-3533.

Abstract

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).