Highly Enantioselective Rhodium‐Catalyzed Addition of Arylboroxines to Simple Aryl Ketones: Efficient Synthesis of Escitalopram. Issue 14 (2nd March 2016)

• Record Type: Journal Article
• Authors: Huang, Linwei; Zhu, Jinbin; Jiao, Guangjun; Wang, Zheng; Yu, Xingxin; Deng, Wei‐Ping; Tang, Wenjun
• Is Part Of: Angewandte Chemie international edition. Volume 55:Issue 14(2016)
• Page Start: 4527
• Page End: 4531
• Publication Date: 2016-03-02
• Subjects: asymmetric catalysis -- enantioselectivity -- ligand design -- rhodium -- total synthesis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201600979
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Highly enantioselective additions of arylboroxines to simple aryl ketones have been achieved for the first time with a Rh/( R, R, R, R )‐WingPhos catalyst, thus providing a range of chiral diaryl alkyl carbinols with excellent ee values and yields. ( R, R, R, R )‐WingPhos has been proven to be crucial for the high reactivity and enantioselectivity. The method has enabled a new, concise, and enantioselective synthesis of the antidepressant drug escitalopram. Abstract : Wing it : The title reaction has been achieved for the first time with a Rh/( R, R, R, R )‐WingPhos catalyst, providing a range of chiral diaryl alkyl carbinols with excellent ee values and yields. The method was applied for a concise synthesis of the antidepressant drug escitalopram. MTBE= tert ‐butyl methyl ether.