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Determination of the absolute stereostructure of a cyclic azobenzene from the crystal structure of the precursor containing a heavy element

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Title: Determination of the absolute stereostructure of a cyclic azobenzene from the crystal structure of the precursor containing a heavy element
Authors: Thomas, Reji Browse this author
Tamaoki, Nobuyuki Browse this author →KAKEN DB
Keywords: azobenzene
cyclic compound
enantiomer
stereostructure
X-ray crystal analysis
Issue Date: 19-Oct-2016
Publisher: Beilstein-Institut
Journal Title: Beilstein journal of organic chemistry
Volume: 12
Start Page: 2211
End Page: 2215
Publisher DOI: 10.3762/bjoc.12.212
Abstract: Single crystal X-ray diffraction has been used as one of the common methods for the unambiguous determination of the absolute stereostructure of chiral molecules. However, this method is limited to molecules containing heavy atoms or to molecules with the possibility of functionalization with heavy elements or chiral internal references. Herein, we report the determination of the absolute stereostructure of the enantiomers of molecule (E)-2, which lacks the possibility of functionalization, using a reverse method, i.e., defunctionalization of its precursor of known stereostructure with bromine substitution (S-(-)-(E)-1). A reductive debromination of S-(-)-(E)-1 results in formation of one of the enantiomers of (E)-2. Using a combination of HPLC and CD spectroscopy we could safely assign the stereostructure of one of the enantiomers of (E)-2, the reduced product R-(-)-(E)-1.
Rights: © 2016 Thomas and Tamaoki; licensee Beilstein-Institut.
http://creativecommons.org/licenses/by/4.0
Type: article
URI: http://hdl.handle.net/2115/63731
Appears in Collections:電子科学研究所 (Research Institute for Electronic Science) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 玉置 信之

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