ABSTRACT
Asymmetric haloetherifications can be conducted using 1,1'-bi-2-naphthol (BINOL) phosphates as catalyst. In combination with simple N-haloamides such as N-iodopyrrolidinone or N-bromosuccinimide, good enantioselectivities can be achieved. However, depending on the substrate, the choice of BINOL phosphate is important, and different catalysts show remarkably different selectivities.
ABSTRACT
The rapid and efficient construction of complex chiral bicyclic amines is possible using a novel alkene diamination reaction. Electrophilic iodinating agents promote the intramolecular anti-selective diamination of alkenes and allow the efficient synthesis of chiral amines such as trans-bipyrrolidines.
Subject(s)
Alkenes/chemistry , Pyrrolidines/chemical synthesis , Amination , Catalysis , Combinatorial Chemistry Techniques , Cyclization , Molecular Structure , Pyrrolidines/chemistry , StereoisomerismABSTRACT
A new approach to enantioselective haloetherification reactions via desymmetrization of in situ-generated meso-halonium ions is described. The combination of N-haloamides as a halogen source and sodium salts of chiral phosphoric acids as catalysts can be used for the cyclization of symmetrical ene-diol substrates, yielding the haloetherification products under practical conditions in enantioenriched form.
