Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 348, Issue 16-17, Pages 2466-2474Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.200600319
Keywords
arynes; asymmetric catalysis; [2+2+2] cycloaddition; helicenes; palladium
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The use of BINAP-based palladium(0) catalysts in the reaction of 7-methoxy-1,2-didehydronaphthalene (2) and dimethyl acetylenedicarboxylate (DMAD) affords non-racemic 9,12-dimethoxypentahelicene I with reasonable ees, among other cycloaddition products. This is the first example of an enantioselective, metal-catalyzed cycloaddition involving arynes.
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