Organic letters

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

MPA Lyle, PD Wilson

Index: Lyle, Michael P. A.; Wilson, Peter D. Organic Letters, 2004 , vol. 6, # 5 p. 855 - 857

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Citation Number: 57

Abstract

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: ...