Enantioselective [4+4] photodimerization of anthracene-2,6-dicarboxylic acid mediated by a C2-symmetric chiral template

Enantioselective [4+4] photodimerization of anthracene-2,6-dicarboxylic acid mediated by a C2-symmetric chiral template

A chiral template was constructed from 7-ethynyl-1,5,7-trimethyl-3-azabicyclo[3.3.1]nonan-2-one by Sonogashira cross-coupling with 4,4''-diiodoterphenyl and was shown to bind the title compound strongly by hydrogen bonding resulting in enantioselectivities of up to 55% enantiomeric excess...

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Veröffentlicht in:Chemical communications (Cambridge, England) England), 2016-01, Vol.52 (5), p.1032-1035
Hauptverfasser: Maturi, Mark M, Fukuhara, Gaku, Tanaka, Koichiro, Kawanami, Yuko, Mori, Tadashi, Inoue, Yoshihisa, Bach, Thorsten
Format: Artikel
Sprache:eng
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Zusammenfassung:A chiral template was constructed from 7-ethynyl-1,5,7-trimethyl-3-azabicyclo[3.3.1]nonan-2-one by Sonogashira cross-coupling with 4,4''-diiodoterphenyl and was shown to bind the title compound strongly by hydrogen bonding resulting in enantioselectivities of up to 55% enantiomeric excess (ee) in the [4+4] anthracene photodimerization.
ISSN:1364-548X
DOI:10.1039/c5cc09107a