Kinetic Resolution of BINAMs by Stereoselective Copper-Catalyzed Dehydrogenative Si–N Coupling with Prochiral Dihydrosilanes
Finn H. Gattwinkel, Martin Oestreich
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.
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.
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Taxonomy
TopicsOrganoboron and organosilicon chemistry · Catalytic C–H Functionalization Methods · Catalytic Cross-Coupling Reactions