TY - JOUR
T1 - C-C Bond Cleavage of Unactivated 2-Acylimidazoles
AU - Xin, Hai Long
AU - Pang, Bo
AU - Choi, Jeesoo
AU - Akkad, Walaa
AU - Morimoto, Hiroyuki
AU - Ohshima, Takashi
N1 - Funding Information:
This work was supported by Grant-in-Aid for Scientific Research on Innovative Areas (JSPS KAKENHI Grant No. JP15H05846 in Middle Molecular Strategy for T.O.) from JSPS, and Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS) (Grant No. JP19am0101091) from AMED, and Takeda Science Foundation. The computation was carried out using the computer resources offered under the category of General Projects by Research Institute for Information Technology, Kyushu University. H.-L.X. acknowledges financial support (2017–2019) from the Otsuka Toshimi Scholarship Foundation. We thank Prof. Katsuhiko Tomooka, Dr. Kazunobu Igawa, and Dr. Yuuya Kawasaki at Kyushu University and DAICEL Corp. for lending us their chiral columns.
Publisher Copyright:
Copyright © 2020 American Chemical Society.
Copyright:
Copyright 2020 Elsevier B.V., All rights reserved.
PY - 2020/9/18
Y1 - 2020/9/18
N2 - 2-Acylimidazoles are widely used as post-Transformable carboxylic acid equivalents in chemoselective and enantioselective reactions. Their transformations, however, require pretreatment with highly reactive, toxic methylating reagents to facilitate C-C bond cleavage. Here, we demonstrate that such pretreatment can be avoided and the C-C bond cleaved under neutral conditions without the use of additional reagents or catalysts. The scope of the reaction, including the use of products reported in the literature as substrates, and some mechanistic insights are described.
AB - 2-Acylimidazoles are widely used as post-Transformable carboxylic acid equivalents in chemoselective and enantioselective reactions. Their transformations, however, require pretreatment with highly reactive, toxic methylating reagents to facilitate C-C bond cleavage. Here, we demonstrate that such pretreatment can be avoided and the C-C bond cleaved under neutral conditions without the use of additional reagents or catalysts. The scope of the reaction, including the use of products reported in the literature as substrates, and some mechanistic insights are described.
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U2 - 10.1021/acs.joc.0c01458
DO - 10.1021/acs.joc.0c01458
M3 - Article
AN - SCOPUS:85092923193
VL - 85
SP - 11592
EP - 11606
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 18
ER -