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

Mark M. Maturi; Gaku Fukuhara; Koichiro Tanaka; Yuko Kawanami; Tadashi Mori; Yoshihisa Inoue; Thorsten Bach

doi:10.1039/c5cc09107a

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

Mark M. Maturi, Gaku Fukuhara, Koichiro Tanaka, Yuko Kawanami, Tadashi Mori, Yoshihisa Inoue, Thorsten Bach

Chair of Organic Chemistry 1

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25 Scopus citations

Abstract

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.

Original language	English
Pages (from-to)	1032-1035
Number of pages	4
Journal	Chemical Communications
Volume	52
Issue number	5
DOIs	https://doi.org/10.1039/c5cc09107a
State	Published - 2016

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

abstract = "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.",

author = "Maturi, \{Mark M.\} and Gaku Fukuhara and Koichiro Tanaka and Yuko Kawanami and Tadashi Mori and Yoshihisa Inoue and Thorsten Bach",

note = "Publisher Copyright: {\textcopyright} The Royal Society of Chemistry 2016.",

year = "2016",

doi = "10.1039/c5cc09107a",

language = "English",

volume = "52",

pages = "1032--1035",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Enantioselective [4+4] photodimerization of anthracene-2,6-dicarboxylic acid mediated by a C2-symmetric chiral template

AU - Maturi, Mark M.

AU - Fukuhara, Gaku

AU - Tanaka, Koichiro

AU - Kawanami, Yuko

AU - Mori, Tadashi

AU - Inoue, Yoshihisa

AU - Bach, Thorsten

PY - 2016

Y1 - 2016

N2 - 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.

AB - 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.

UR - https://www.scopus.com/pages/publications/84954063694

U2 - 10.1039/c5cc09107a

DO - 10.1039/c5cc09107a

M3 - Article

AN - SCOPUS:84954063694

SN - 1359-7345

VL - 52

SP - 1032

EP - 1035

JO - Chemical Communications

JF - Chemical Communications

IS - 5

ER -

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

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