title: Highly Enantioselective Rhodium-Catalyzed Addition of Arylboroxines to Simple Aryl Ketones: Efficient Synthesis of Escitalopram.
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.
authors.affiliation: Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Mei Long Rd, Shanghai, 200237, China.
authors.forename: Linwei
authors.initials: L
authors.lastname: Huang
authors.affiliation: Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Mei Long Rd, Shanghai, 200237, China.
authors.forename: Jinbin
authors.initials: J
authors.lastname: Zhu
authors.affiliation: State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China.
authors.forename: Guangjun
authors.initials: G
authors.lastname: Jiao
authors.affiliation: Innovation Center China, AstraZeneca Global R&D, China.
authors.forename: Zheng
authors.initials: Z
authors.lastname: Wang
authors.affiliation: Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Mei Long Rd, Shanghai, 200237, China.
authors.forename: Xingxin
authors.initials: X
authors.lastname: Yu
authors.affiliation: Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Mei Long Rd, Shanghai, 200237, China. weiping_deng@ecust.edu.cn.
authors.forename: Wei-Ping
authors.initials: WP
authors.lastname: Deng
authors.affiliation: Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Mei Long Rd, Shanghai, 200237, China. tangwenjun@sioc.ac.cn.|State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032, China. tangwenjun@sioc.ac.cn.
authors.forename: Wenjun
authors.initials: W
authors.lastname: Tang
mesh_terms: D001896:Boron Compounds / Q000737:chemistry*; D002384:Catalysis; D015283:Citalopram / Q000138:chemical synthesis*; D007659:Ketones / Q000737:chemistry*; D012238:Rhodium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D001896:Boron Compounds; D007659:Ketones; D015283:Citalopram; D012238:Rhodium
keywords: asymmetric catalysis; enantioselectivity; ligand design; rhodium; total synthesis