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Enantioselective Rhodium‐Catalyzed Addition of Arylboroxines to N‐Unprotected Ketimines: Efficient Synthesis of Cipargamin
Author(s) -
Zhu Jinbin,
Huang Linwei,
Dong Wei,
Li Naikai,
Yu Xingxin,
Deng WeiPing,
Tang Wenjun
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201910008
Subject(s) - enantioselective synthesis , rhodium , catalysis , chemistry , trifluoromethyl , ligand (biochemistry) , combinatorial chemistry , organic chemistry , biochemistry , alkyl , receptor
Highly enantioselective rhodium‐catalyzed addition of arylboroxines to N‐unprotected ketimines is realized for the first time by employing chiral BIBOP‐type ligands with a Rh loading as low as 1 mol %. A range of chiral α‐trifluoromethyl‐α,α‐diaryl α‐tertiary amines or 3‐amino‐3‐aryloxindoles were formed with excellent ee values and yields by employing either WingPhos or PFBO‐BIBOP as the ligand. The method has enabled an efficient enantioselective synthesis of cipargamin.