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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Authors: | Lyle Michael P A Wilson Peter D |
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Institution: | Department of Chemistry, Simon Fraser University, 8888 University Drive, Burnaby, British Columbia, Canada V5A 1S6. |
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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 (>95:5 dr and up to 99% ee). These are the highest reported stereoselectivities for a chiral bipyridyl ligand. structure: see text] |
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