Journal
ORGANIC LETTERS
Volume 23, Issue 7, Pages 2421-2425Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00270
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Funding
- National Natural Science Foundation of China [21903072, 21773214, 21822303, 21772020]
- 111 Project [D20003, 2020GGJS016]
- National Supercomputing Center in Zhengzhou
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Desymmetrizing reactions of olefins catalyzed by N-Heterocyclic carbene (NHC) have been rapidly developing, but the origins of the chemo- and stereoselectivities in these reactions are still poorly understood. This study proposes a mechanistic map to predict how these selectivities are controlled by different active intermediates and contradicts a previous proposition regarding the determination of product structures by a transformation between a pair of isomers.
N-Heterocyclic carbene (NHC) catalyzed desymmetrizing reactions of olefins have rapidly developed in recent years; however, the origins of the chemo- and stereoselectivities of these reactions remain poorly understood. Herein, we propose a mechanistic map for these reactions to predict how chemo- and stereoselectivities are controlled by different active intermediates (i.e., Breslow and acylazolium intermediates). Remarkably, our findings contradict a previous proposition that product structures are determined by a transformation between a pair of isomers.
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