@article{44606e7ca5d644a8991fcb5729d262d4,
title = "Highly Regioselective 5-endo-tet Cyclization of 3,4-Epoxy Amines into 3-Hydroxypyrrolidines Catalyzed by La(OTf)3",
abstract = "Highly regioselective intramolecular aminolysis of 3,4-epoxy amines has been achieved. Key features of this reaction are (1) chemoselective activation of epoxides in the presence of unprotected aliphatic amines in the same molecules by a La(OTf)3 catalyst and (2) excellent regioselectivity for anti-Baldwin 5-endo-tet cyclization. This reaction affords 3-hydroxy-2-alkylpyrrolidines stereospecifically in high yields. DFT calculations revealed that the regioselectivity might be attributed to distortion energies of epoxy amine substrates. The use of this reaction was demonstrated by the first enantioselective synthesis of an antispasmodic agent prifinium bromide.",
keywords = "amines, chemoselectivity, cyclization, regioselectivity, synthetic methods",
author = "Yuse Kuriyama and Yusuke Sasano and Yoshihiko Hoshino and Uesugi, {Shun ichiro} and Aoto Yamaichi and Yoshiharu Iwabuchi",
note = "Funding Information: This work was partially supported by JSPS KAKENHI Grant Nos. 18H04232 (Precisely Designed Catalysts with Customized Scaffolding), and 19H03347 and by Platform Project for Supporting Drug Discovery and Life Science Research [Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)] from AMED under Grant No. JP18am0101100. We thank Prof. Toshinobu Korenaga (Iwate University) for useful discussion. Funding Information: This work was partially supported by JSPS KAKENHI Grant Nos. 18H04232 (Precisely Designed Catalysts with Customized Scaffolding), and 19H03347 and by Platform Project for Supporting Drug Discovery and Life Science Research [Basis for Supporting Innovative Drug Discovery and Life Science Research (BINDS)] from AMED under Grant No. JP18am0101100. We thank Prof. Toshinobu Korenaga (Iwate University) for useful discussion. Publisher Copyright: {\textcopyright} 2020 Wiley-VCH GmbH",
year = "2021",
month = jan,
day = "26",
doi = "10.1002/chem.202004455",
language = "English",
volume = "27",
pages = "1961--1965",
journal = "Chemistry - A European Journal",
issn = "0947-6539",
publisher = "Wiley-VCH Verlag",
number = "6",
}