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

Caeiro Jorge | Zendy; Peña Diego | Zendy; Cobas Agustín | Zendy; Pérez Dolores | Zendy; Guitián Enrique | Zendy

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

Author(s) -

Caeiro Jorge,

Peña Diego,

Cobas Agustín,

Pérez Dolores,

Guitián Enrique

Publication year - 2006

Publication title -

advanced synthesis and catalysis

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.541

H-Index - 155

eISSN - 1615-4169

pISSN - 1615-4150

DOI - 10.1002/adsc.200600319

Subject(s) - enantioselective synthesis , cycloaddition , chemistry , aryne , dimethyl acetylenedicarboxylate , catalysis , organic chemistry , combinatorial chemistry , medicinal chemistry

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 ee s, among other cycloaddition products. This is the first example of an enantioselective, metal‐catalyzed cycloaddition involving arynes.

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