Enantioselective Rhodium‐Catalyzed Addition of Arylboroxines to N‐Unprotected Ketimines: Efficient Synthesis of Cipargamin. Issue 45 (24th September 2019)

• Record Type: Journal Article
• Authors: Zhu, Jinbin; Huang, Linwei; Dong, Wei; Li, Naikai; Yu, Xingxin; Deng, Wei‐Ping; Tang, Wenjun
• Is Part Of: Angewandte Chemie international edition. Volume 58:Issue 45(2019)
• Page Start: 16119
• Page End: 16123
• Publication Date: 2019-09-24
• Subjects: asymmetric catalysis -- enantioselectivity -- ketimines -- P ligands -- rhodium; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201910008
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: 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. Abstract : Wing it : 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 in excellent yields by employing either WingPhos or PFBO‐BIBOP as the ligand. The method enabled an efficient enantioselective synthesis of cipargamin.