Highly Enantioselective Rhodium-Catalyzed Addition of Arylboroxines to Simple Aryl Ketones: Efficient Synthesis of Escitalopram
Linwei Huang
Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Mei Long Rd, Shanghai, 200237 China
Search for more papers by this authorJinbin Zhu
Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Mei Long Rd, Shanghai, 200237 China
Search for more papers by this authorGuangjun Jiao
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032 China
Search for more papers by this authorDr. Zheng Wang
Innovation Center China, AstraZeneca Global R&D, China
Search for more papers by this authorProf. Dr. Xingxin Yu
Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Mei Long Rd, Shanghai, 200237 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Wei-Ping Deng
Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Mei Long Rd, Shanghai, 200237 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Wenjun Tang
Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Mei Long Rd, Shanghai, 200237 China
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032 China
Search for more papers by this authorLinwei Huang
Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Mei Long Rd, Shanghai, 200237 China
Search for more papers by this authorJinbin Zhu
Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Mei Long Rd, Shanghai, 200237 China
Search for more papers by this authorGuangjun Jiao
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032 China
Search for more papers by this authorDr. Zheng Wang
Innovation Center China, AstraZeneca Global R&D, China
Search for more papers by this authorProf. Dr. Xingxin Yu
Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Mei Long Rd, Shanghai, 200237 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Wei-Ping Deng
Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Mei Long Rd, Shanghai, 200237 China
Search for more papers by this authorCorresponding Author
Prof. Dr. Wenjun Tang
Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Mei Long Rd, Shanghai, 200237 China
State Key Laboratory of Bio-Organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, 200032 China
Search for more papers by this authorGraphical 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.
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.
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