Premium
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.