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DOI: 10.1055/a-1961-6102
Catalytic Enantioselective Dihalogenation of Alkenes
This research was supported by the China Postdoctoral Science Foundation (2020M682280). We also thank the National Natural Science Foundation of China (NSFC, grant nos. 22071149 and 21871178), and the Science and Technology Commission of Shanghai Municipality (STCSM, grant no. 19JC1430100) for financial support. This research was also supported by The Program for Professor of Special Appointment (Eastern Scholar) at Shanghai Institutions of Higher Learning.
Abstract
Vicinal dihalides not only emerge as reactive intermediates in synthetic organic chemistry, but also are extensively existing in bioactive marine natural products. The dihalogenation of alkenes is the most direct and effective method for the synthesis of vicinal dihalides. Because there is always an exchange process between the chiral haloniums and the unreacted olefins to cause racemization, the development of catalytic enantioselective dihalogenation of alkenes is of great difficulty. Recently, great progress has been made in catalytic asymmetric manner. However, there is a lack of related review of discussions of the mechanisms and reaction systems. This review is aimed at summarizing enantioselective dihalogenation of alkenes, including 1,2-dichlorination, 1,2-dibromination, and 1,2-difluorination, which is expected to encourage more researchers to participate in this field.
1 Introduction
2 Enantioselective 1,2-Dichlorination and 1,2-Dibromination of Alkenes
2.1 Chiral-Boron-Complex-Promoted Enantioselective 1,2-Dichlorination
2.2 Organocatalytic Asymmetric 1,2-Dichlorination and 1,2-Dibromination
2.3 Chiral-Titanium-Complex-Catalyzed 1,2-Dihalogenation
3 Chiral-Iodide-Catalyzed Enantioselective Oxidative 1,2-Difluorination
4 Summary and Outlook
Publication History
Received: 02 July 2022
Accepted after revision: 14 October 2022
Accepted Manuscript online:
14 October 2022
Article published online:
24 October 2022
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For selected reviews, see:
A strategy to create asymmetric environment on substrate using cyclodextrins etc. was reported by Tanaka and co-workers from 1983 on. Here we won’t go into too much detail. See: