Hodgson, David M. Mortimer, Claire L. McKenna, Jeffrey M. Amine Protection/α-Activation with the <i>tert</i>-Butoxythiocarbonyl Group: Application to Azetidine Lithiation–Electrophilic Substitution <i>tert</i>-Butoxythiocarbonyl (Botc), the long-neglected thiocarbonyl analogue of Boc, facilitates (unlike its alkoxycarbonyl cousin) α-lithiation and electrophile incorporation on <i>N</i>-Botc-azetidine. <i>N</i>,<i>N</i>,<i>N</i>′,<i>N</i>′-<i>endo</i>,<i>endo</i>-Tetramethyl-2,5-diaminonorbornane proved optimal as a chiral ligand, generating adducts with er up to 92:8. Facile deprotection, under conditions that left the corresponding <i>N</i>-Boc systems intact, was achieved using either TFA or via thermolysis in ethanol. adduct;electrophile incorporation;Application;analogue;Lithiation;thermolysi;chiral ligand;deprotection;Facile;Protection;lithiation;Botc;ethanol;Boc;TFA;Azetidine;Amine;thiocarbonyl;alkoxycarbonyl cousin 2015-12-17
    https://acs.figshare.com/articles/journal_contribution/Amine_Protection_Activation_with_the_i_tert_i_Butoxythiocarbonyl_Group_Application_to_Azetidine_Lithiation_Electrophilic_Substitution/2047257
10.1021/ol503441d.s001