S. De Vries, Timothy Majumder, Supriyo Sandelin, Angela M. Wang, Guoqiang Vedejs, Edwin Mechanistic Variations in Ionic Hydrogenation of Unsaturated Phosphine and Amine Boranes Internal hydride transfer occurs when tethered carbocations are generated from unsaturated phosphine or phosphinite boranes. 3-Methylenecyclohexyl-derived boranes <b>12</b> or <b>18</b> react with MsOH to give ionic hydrogenation products with high <i>syn</i>-selectivity. With unsaturated amine boranes, initial hydrogen evolution gives BH<sub>2</sub>(OMs) complexes, but IH occurs using excess MsOH in a slower second stage. A diastereoselective reaction occurs from <b>26b</b> using camphorsulfonic acid (first stage) and MsOH (second stage), affording 33 (68% ee) after hydrolysis. Ionic Hydrogenation;hydrogenation products;BH;hydrogen evolution;MsOH;camphorsulfonic acid;Mechanistic Variations;phosphinite boranes;Amine BoranesInternal hydride transfer;diastereoselective reaction;amine boranes;26 b;IH;Unsaturated Phosphine 2012-02-03
    https://acs.figshare.com/articles/journal_contribution/Mechanistic_Variations_in_Ionic_Hydrogenation_of_Unsaturated_Phosphine_and_Amine_Boranes/2553637
10.1021/ol2031203.s001