461031-82-3Relevant articles and documents
On the verge of axial chirality: Atroposelective synthesis of the AB-biaryl fragment of vancomycin
Bringmann, Gerhard,Menche, Dirk,Muehlbacher, Joerg,Reichert, Matthias,Saito, Nozomi,Pfeiffer, Steven S.,Lipshutz, Bruce H.
, p. 2833 - 2836 (2007/10/03)
(figure presented) Using the "lactone concept", differently substituted AB-biaryl fragments (P)-2 (R = Me, t-Bu) of vancomycin have been synthesized atroposelectively. Their otherwise configurational instability was remedied by inclusion of two chlorine atoms in the B ring to give (M)-29. Starting from a still configurationally unstable lactone-bridged precursor, we obtained this biaryl with high atroposelectivity (dr 94:6) by ring cleavage with dynamic kinetic diastereomeric resolution.