# Kinetic Resolution of BINAMs by Stereoselective Copper-Catalyzed Dehydrogenative Si–N Coupling with Prochiral Dihydrosilanes

## TL;DR

A new method for separating BINAM molecules using copper-catalyzed reactions with chiral ligands is developed, enabling efficient resolution with good selectivity.

## Contribution

A stereoselective Cu–H-catalyzed dehydrogenative Si–N coupling method for kinetic resolution of BINAMs is introduced.

## Key findings

- The method allows atroposelective and diastereoselective N-silylation of BINAMs.
- BINAMs with substituents in 6,6′- or 7,7′-positions are resolved with good selectivity factors.
- The use of (R,R)-Ph-BPE as a chiral ligand is key to achieving stereoselectivity.

## Abstract

A nonenzymatic kinetic
resolution of monoprotected 1,1′-binaphthyl-2,2′-diamine
(BINAM) derivatives is reported. This is achieved by a Cu–H-catalyzed
dehydrogenative Si–N coupling with prochiral dihydrosilanes
using (R,R)-Ph-BPE as a chiral ligand.
The atroposelective as well as diastereoselective N-silylation enables the resolution of BINAMs with various substituents
in 6,6′- or 7,7′-positions with good to synthetically
useful selectivity factors.