Pulis, Alexander P. Aggarwal, Varinder K. Synthesis of Enantioenriched Tertiary Boronic Esters from Secondary Allylic Carbamates. Application to the Synthesis of C30 Botryococcene Enantioenriched secondary allylic carbamates have been deprotonated with <i>s</i>BuLi and reacted with boronic esters. In contrast to other electrophiles, high α-selectivity was observed and the boronate complexes were formed with almost complete retention of stereochemistry. The boronate complexes underwent a stereospecific 1,2-migration leading to tertiary allylic boronic esters with high <i>er</i> (>98:2). The scope of the reaction has been explored and found to embrace a broad range of both allylic carbamates and boronic esters. The methodology has been applied to an eight-step, stereoselective synthesis of each of the diastereoisomers of C30 botryococcene. boronic esters;C 30 BotryococceneEnantioenriched;allylic boronic esters;Secondary Allylic Carbamates;C 30 botryococcene;Enantioenriched Tertiary Boronic Esters;boronate complexes;Synthesi;allylic carbamates 2012-05-02
    https://acs.figshare.com/articles/journal_contribution/Synthesis_of_Enantioenriched_Tertiary_Boronic_Esters_from_Secondary_Allylic_Carbamates_Application_to_the_Synthesis_of_C30_Botryococcene/2526895
10.1021/ja303022d.s002