Asymmetric 1,3‐Dipolar Cycloaddition Reactions of Enones by Primary Amine Catalysis

Yang, Qi; Zhang, Jieyu; Jia, Zongbin; Yang, Chunming; Zhang, Long; Luo, Sanzhong

doi:10.1002/ajoc.201900013

Cited by 5 publications

(1 citation statement)

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“…Representative examples include the cyclopropanation of acroleins with α ‐diazoesters, 1,3‐dipolar cycloaddition between cyclic enones and nitrones. [ 57‐58 ] In 2018, our group reported the desymmetrizing dehydrogenation of 4‐subsituted cyclohexanones through enamine oxidative catalysis with IBX as the oxidant. [ 59 ] This protocol can be combined with iminium ion catalysis to enable asymmetric β ‐C—H functionalization of ketone with various nucleophiles.…”

Section: Bi/multi‐function Strategy: Development and Application Of C...mentioning

confidence: 99%

Bio‐inspired Small Molecular Catalysis

2022

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Comprehensive Summary Nature is an inspiring resource for chemists to exploit uncharted chemical spaces. Enzymes in nature are characteristic of high efficiency and exquisite stereocontrol under rather mild conditions. Not surprisingly, chemists have a long history in developing new catalysts by learning from and imitating the natural enzymes. This review summarizes our long‐standing efforts in developing bio‐inspired small molecular catalysis. These were categorized according to the employed strategies: 1) bi‐/multi‐functional strategy for the bio‐inspired chiral primary amine catalyst; 2) cofactor strategy for bio‐inspired ortho‐quinone catalyst; 3) intermediate strategy for chiral latent carbocation catalysis based on natural carbocation process. Each section includes brief introduction of the biological origin, design of catalyst, development of methodology as well as the underlying mechanistic insights. What is the most favorite and original chemistry developed in your research group? I hope it's always the next one. How do you get into this specific field? Could you please share some experiences with our readers? Nature provides many astonishing catalytic machineries for building up molecular complexity and harnessing energy in the most efficient ways. Nature's recipe for catalysis serves as a starting point to develop new catalyst for synthetic and energy chemistry. I was trained as a synthetic chemist in a physical organic group in Nankai and ICCAS, and spent part of my graduate studies doing enzymatic synthesis of oligosaccharide and its related biological applications in Ohio State University. This gave me a mixed view on organocatalysis, then under its golden stage of renaissance, not only for its synthetic potentials as a new catalytic concept, but also with an eye on its biological origin and possible impact beyond synthesis. I also benefit a lot from the physical organic chemistry training which helps to shape my research path in width and depth, in a way I never imagined and expected at the beginning of my career. How do you supervise your students? Try to inspire beyond instruct. I learned and am still learning. “因材施教” is easy to say than to do. In reality, I become bossy the way I dislike and have to instruct heavily. What is the most important personality for scientific research? Curiosity, broad reading and sufficient “free time” for daydreaming. In order to have enough time to waste, you have to work really hard at first. Who influences you mostly in your life? My Ph.D. supervisor, Prof. Jin‐Pei Cheng who teaches me a rational and quantitative view for chemistry and inspires me all the time to pursue a rational approach in research.

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Section: Bi/multi‐function Strategy: Development and Application Of C...mentioning

confidence: 99%