KHMDS/三甘醇冠醚作为磷杂环戊二烯碱基在使用 HFC-125 的 -亚磺酰亚胺的立体发散五氟乙基化反应中的替代物。
KHMDS/Triglyme Cryptate as an Alternative to Phosphazene Base in Stereodivergent Pentafluoroethylation of -Sulfinylimines Using HFC-125.
机构信息
Department of Life Science and Applied Chemistry, Nagoya Institute of Technology, Gokiso, Showa-Ku, Nagoya 466-8555, Japan.
Department of Nanopharmaceutical Sciences, Nagoya Institute of Technology, Gokiso, Showa-Ku, Nagoya 466-8555, Japan.
出版信息
J Org Chem. 2022 Dec 2;87(23):15806-15819. doi: 10.1021/acs.joc.2c01821. Epub 2022 Oct 31.
A protocol for the stereodivergent pentafluoroethylation of -sulfinylimines using HFC-125 with KHMDS/triglyme has been developed. Both diastereomers of the pentafluoroethylated amines can be selectively synthesized based on the presence or absence of triglyme. This additive-controlled protocol allows the KHMDS/triglyme cryptate to be a straightforward and cheap alternative to previously reported base-controlled stereodivergent trifluoromethylation using potassium hexamethyldisilazide (KHMDS) versus P-Bu.
已经开发出一种使用 HFC-125 和 KHMDS/triglyme 的对 -亚磺酰亚胺进行立体发散五氟乙基化的方案。根据是否存在三甘醇，可以选择性地合成五氟乙基化胺的两种非对映异构体。这种添加剂控制的方案使得 KHMDS/triglyme 配合物成为一种简单且廉价的替代物，替代了先前使用六甲基二硅氮烷钾（KHMDS）与 P-Bu 进行的基于碱控制的立体发散三氟甲基化反应。
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