Catalytic Enantioselective Dihalogenation of Alkenes

Dong, Jiawei; Cao, Ren-Fei; Chen, Zhi Min

doi:10.1055/a-1961-6102

Cited by 2 publications

(2 citation statements)

References 38 publications

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“…9 Recent advances in the catalytic enantioselective dihalogenation of alkenes have been summarized (J.-W. Dong & Z.-M. Chen). 10 The development of kinetic resolution and desymmetrization of amines through nonenzymatic asymmetric catalytic approaches in the last two decades has also been systematically summarized in this cluster (X. Yang). 11 Recent progress on the Brønsted acid catalyzed intramolecular and intermolecular alkyne alkoxylation/Claisen rearrangement has been discussed (L. Li & L.-W. Ye).…”

Section: Cluster Synlettmentioning

confidence: 99%

Cluster Preface: Development and Applications of Novel Ligands/Catalysts and Mechanistic Studies on Catalysis

Zhang

Zhao

2022

Synlett

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Zhipeng Zhang (left) received his B.S. degree from Shandong University (China) in 2004, and his Ph.D. degree from the Shanghai Institute of Organic Chemistry (SIOC) in 2010 under the supervision of Professor Kuiling Ding. In 2011, he began his postdoctoral studies with Professor Benjamin List at the Max Planck Institute for Coal Research in Mülheim an der Ruhr, Germany. After three years of research on asymmetric organocatalysis, he joined the group of Professor Jin-Quan Yu at The Scripps Research Institute in La Jolla, California as a postdoctoral research associate in 2014. He subsequently worked at the Genomics Institute of the Novartis Research Foundation (GNF) from 2016, before he began his independent career as a professor at the East China University of Science and Technology (ECUST) in 2017. His current research interests include asymmetric catalysis and synthetic methodology, focusing on the design and development of novel chiral ligands and catalysts. Baoguo Zhao (right) received his B.S. degree from Wuhan University in 1996, his M.S. degree from Nanjing University under the supervision of Professor Jianhua Xu in 2002, and his Ph.D. degree from the Shanghai Institute of Organic Chemistry (SIOC) under the supervision of Professor Kuiling Ding in 2006. He subsequently worked with Professor Yian Shi for five years as a postdoctoral fellow at the Department of Chemistry of Colorado State University. In 2011, he joined Shanghai Normal University at the Department of Chemistry as a full professor. His current research interests are in the area of biomimetic asymmetric catalysis, including the development of bioinspired chiral catalysts and synthetic methodologies.

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Section: Cluster Synlettmentioning

confidence: 99%

Cluster Preface: Development and Applications of Novel Ligands/Catalysts and Mechanistic Studies on Catalysis

Zhang

Zhao

2022

Synlett

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“…With the advent of numerous methodologies for the asymmetric halofunctionalization of alkenes in recent years, several research groups have unveiled useful protocols for highly asymmetric catalytic alkene dihalogenation through the elegant rationalization of chiral catalysts, in connection with the compatibility of dihalogenating reagents . Both chiral organocatalysts and metal complex catalysts enabled enantioselective homodihalogenation (Scheme b) and heterodihalogenation (Scheme c) of alkenes.…”

Section: Introductionmentioning

confidence: 99%

Enantioselective anti-Dihalogenation of Electron-Deficient Olefin: A Triplet Halo-Radical Pylon Intermediate

Zhang

Liu

et al. 2023

J. Am. Chem. Soc.

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The textbook alkene halogenation reaction establishes straightforward access to vicinal dihaloalkanes. However, a robust catalytic method for dihalogenizing electron-deficient olefins in an enantioselective manner is still under development, and its mechanism remains controversial. Herein, we disclose efficient regio-, anti-diastereo-, and enantioselective dibromination, bromochlorination, and dichlorination reactions of enones catalyzed by a chiral N,N’-dioxide/Yb(OTf)3 complex. With the combination of electrophilic halogen and halide salts as halogenating agents, an array of homo- and heterodihalogenated derivatives is achieved in moderate to good enantioselectivities. Moreover, DFT calculations reveal that a novel triplet halo-radical pylon intermediate is probable in accounting for the exclusive regio- and anti-diastereoselectivity.

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Catalytic Enantioselective Dihalogenation of Alkenes

Cited by 2 publications

References 38 publications

Cluster Preface: Development and Applications of Novel Ligands/Catalysts and Mechanistic Studies on Catalysis

Cluster Preface: Development and Applications of Novel Ligands/Catalysts and Mechanistic Studies on Catalysis

Enantioselective anti-Dihalogenation of Electron-Deficient Olefin: A Triplet Halo-Radical Pylon Intermediate

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