Ir-Catalyzed Allylic Amination and Etherification

Key words

allylic amination - phosphoramidite - iridium

Significance

This system allows for highly ste­reoselective intramolecular allylic aminations and etherifications as well as intermolecular allylic amination followed by intramolecular cyclization (shown). Low catalyst loading (2 mol%), and fast reaction times make this a suitable system for the synthesis of various ring sized N-heterocycles.

Comment

The versatility of this system is exceptional. Application for the synthesis of useful chiral N-heterocycles, O-heterocycles, and allylic amines, all important building blocks, makes this protocol potentially very useful. The ability to form various ring sizes, as well as simple allylic amination, shows the effectiveness of this scheme. Particularly noteworthy is that several useful chiral C-2 symmetric amines can be synthesized enantio­selectively. Previously, these compounds were prepared via a number of steps.