4.7 Article

Catalytic Asymmetric Bromine-Lithium Exchange: A New Tool to Build Axial Chirality

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 352, Issue 14-15, Pages 2611-2620

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201000517

Keywords

asymmetric catalysis; atropoisomerism; biaryls; diphosphines; metal-halogen exchange

Funding

  1. Swiss National Science Foundation [200020-126663]

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We present here the first catalytic desymmetrization of the 2,2',6,6'-tetrabromobiphenyl 1 and analogues, by a bromine-lithium exchange catalyzed by either diamines or diether derivatives (0.5 equiv.), yielding axially chiral compounds in high yield (up to 89%) and high enantioselectivity (up to 82%).

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