Synthesis of a New Chiral Nonracemic C 2-Symmetric 2,2‘-Bipyridyl Ligand and Its Application in Copper(I)-Catalyzed Enantioselective Cyclopropanation Reactions

Synthesis of a New Chiral Nonracemic C 2-Symmetric 2,2‘-Bipyridyl Ligand and Its Application in Copper(I)-Catalyzed Enantioselective Cyclopropanation Reactions

An efficient synthesis of a low molecular weight, chiral nonracemic and C 2-symmetric bipyridyl ligand is reported. The ligand was prepared using a catalytic asymmetric dihydroxylation reaction of a pyrindine as a key step. The ligand was evaluated in the asymmetric copper(I)-catalyzed cyclopropanat...

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Veröffentlicht in:Organic letters 2004-03, Vol.6 (5), p.855-857
Hauptverfasser: Lyle, Michael P. A, Wilson, Peter D
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description An efficient synthesis of a low molecular weight, chiral nonracemic and C 2-symmetric bipyridyl ligand is reported. The ligand was prepared using a catalytic asymmetric dihydroxylation reaction of a pyrindine as a key step. The ligand was evaluated in the asymmetric copper(I)-catalyzed cyclopropanation reactions of a series of alkenes and diazoesters. Very high diastereoselectivities and enantioselectivities were observed (>95:5 dr and up to 99% ee). These are the highest reported stereoselectivities for a chiral bipyridyl ligand.
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title Synthesis of a New Chiral Nonracemic C 2-Symmetric 2,2‘-Bipyridyl Ligand and Its Application in Copper(I)-Catalyzed Enantioselective Cyclopropanation Reactions
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