TY - JOUR
T1 - Iodine-Catalyzed Synthesis of Chiral 4-Imidazolidinones Using α-Amino Acid Derivatives via Dehydrogenative N-H/C(sp3)-H Coupling
AU - Kanyiva, Kyalo Stephen
AU - Tane, Marina
AU - Shibata, Takanori
N1 - Funding Information:
We thank Ms. Shen Wenyin (Waseda University) for some initial experiments. This work was supported financially by a Grant-in-Aid for Scientific Research (C) (no. 18K05114) from JSPS and Waseda University grants for Special Research Projects (2018K-296 and 2018B-200).
Publisher Copyright:
© 2019 American Chemical Society.
PY - 2019/10/18
Y1 - 2019/10/18
N2 - An efficient method for the asymmetric synthesis of 4-imidazolidinones via an iodine-catalyzed intramolecular N-H/C(sp3)-H activation of readily available and abundant feedstocks, amino acids, and amines is described. The reaction proceeded under visible light irradiation to afford a variety of 4-imidazolidinone derivatives under mild conditions in moderate to excellent yields. Secondary and tertiary C(sp3)-H bonds were aminated, and various functional groups were tolerated.
AB - An efficient method for the asymmetric synthesis of 4-imidazolidinones via an iodine-catalyzed intramolecular N-H/C(sp3)-H activation of readily available and abundant feedstocks, amino acids, and amines is described. The reaction proceeded under visible light irradiation to afford a variety of 4-imidazolidinone derivatives under mild conditions in moderate to excellent yields. Secondary and tertiary C(sp3)-H bonds were aminated, and various functional groups were tolerated.
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U2 - 10.1021/acs.joc.9b01154
DO - 10.1021/acs.joc.9b01154
M3 - Article
C2 - 31313588
AN - SCOPUS:85071718471
VL - 84
SP - 12773
EP - 12783
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 20
ER -