Asymmetric Catalysis in the [2+2+2] Cycloaddition of Arynes and Alkynes: Enantioselective Synthesis of a Pentahelicene

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 1 with reasonable ees, among other cycloaddition products. This is the first example of an enantioselecti...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2006-11, Vol.348 (16-17), p.2466-2474
Main Authors: Caeiro, Jorge, Peña, Diego, Cobas, Agustín, Pérez, Dolores, Guitián, Enrique
Format: Article
Language:English
Subjects:
[2+2+2] cycloaddition
arynes
asymmetric catalysis
helicenes
palladium
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Summary: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 1 with reasonable ees, among other cycloaddition products. This is the first example of an enantioselective, metal‐catalyzed cycloaddition involving arynes.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.200600319