783333-05-1Relevant academic research and scientific papers
Transition Metal Free C-N Bond Forming Dearomatizations and Aryl C-H Aminations by in Situ Release of a Hydroxylamine-Based Aminating Agent
Farndon, Joshua J.,Ma, Xiaofeng,Bower, John F.
, p. 14005 - 14008 (2017/10/17)
We outline a simple protocol that accesses directly unprotected secondary amines by intramolecular C-N bond forming dearomatization or aryl C-H amination. The method is dependent on the generation of a potent electrophilic aminating agent released by in situ deprotection of O-Ts activated N-Boc hydroxylamines.
Synthesis of chiral chromans by the Pd-catalyzed asymmetric allylic alkylation (AAA): Scope, mechanism, and applications
Trost, Barry M.,Shen, Hong C.,Dong, Li,Surivet, Jean-Philippe,Sylvain, Catherine
, p. 11966 - 11983 (2007/10/03)
The Pd-catalyzed asymmetric allylic alkylation (AAA) of phenol allyl carbonates serves as an efficient strategy to construct the allylic C-O bond allowing access to chiral chromans in up to 98% ee. The effect of pH and the influence of olefin geometry, as well as substitution pattern on the ee and the absolute configuration of the chiral chromans were explored in detail. These observations suggest a mechanism involving the cyclization of the more reactive π-allyl palladium diastereomeric intermediate as the enantiodiscriminating step (Curtin-Hammett conditions). This methodology led to the enantioselective synthesis of the vitamin E core, the first enantioselective total synthesis of (+)-clusifoliol and (-)-siccanin, and the synthesis of an advanced intermediate toward (+)-rhododaurichromanic acid A.
