10.1021/ol026182e.s001 Gerhard Bringmann Gerhard Bringmann Dirk Menche Dirk Menche Jörg Mühlbacher Jörg Mühlbacher Matthias Reichert Matthias Reichert Nozomi Saito Nozomi Saito Steven S. Pfeiffer Steven S. Pfeiffer Bruce H. Lipshutz Bruce H. Lipshutz On the Verge of Axial Chirality:  Atroposelective Synthesis of the AB-Biaryl Fragment of Vancomycin<sup>†</sup><sup>,</sup><sup>‡</sup> American Chemical Society 2002 inclusion atroposelectivity Chirality Axial concept biaryl vancomycin chlorine atoms Fragment dr atroposelectively Bu B ring lactone Synthesi configurationally Atroposelective fragment diastereomeric resolution configurational instability ring cleavage Vancomycin precursor Verge 2002-07-27 00:00:00 Journal contribution https://acs.figshare.com/articles/journal_contribution/On_the_Verge_of_Axial_Chirality_Atroposelective_Synthesis_of_the_AB-Biaryl_Fragment_of_Vancomycin_sup_sup_sup_sup_sup_sup_/3743205 Using the “lactone concept”, differently substituted AB-biaryl fragments (<i>P</i>)-2 (R = Me, <i>t</i>-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 (<i>M</i>)-<b>29</b>. 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.