Enantioselective Synthesis of 3-Azabicyclo[4.1.0]heptenes and 3-Azabicyclo[3.2.0]heptenes by Ir-Catalyzed Asymmetric Allylic Amination of N-Tosyl Propynylamine and Pt-Catalyzed Cycloisomerization

摘要

Irresistible! Highly regio- and enantioselective Ir-catalyzed allylic amination reactions of N-tosyl propynylamines have been realized. The resulting N-tosyl allylpropynylamines were transformed into highly enantioenriched 3-azabicyclo[4.1.0]heptenes and 3-azabicyclo[3.2.0]heptenes, respectively, in the presence of PtCl₂ (see scheme; Ts=tosyl, cod=1,5-cyclooctadiene, TBAF=tetrabutylammonium fluoride, TMS=trimethylsilyl).