Catalytic Asymmetric Addition and Telomerization of Butadiene with Enamine Intermediates

Wang, Yaning; Zhang, Jie; You, Chang; Mi, Xueling; Luo, Sanzhong

doi:10.31635/ccschem.021.202101240

Cited by 15 publications

(6 citation statements)

References 58 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…At the same time, β-ketocarbonyl compound 1a combines with amino catalyst to form enamine intermediate ( IV ), which then coupled with the Rh-π-allyl species ( III ) to give the allylation product after hydrolysis. The observed stereoselectivity could be explained by the steric model. , It is known that the regioselectivity of the reaction is a result of joint influence by the ligand bite angle and the steric interactions . Similar linear addition was observed with BINAP/Rh .…”

mentioning

confidence: 99%

See 1 more Smart Citation

Asymmetric Coupling of β-Ketocarbonyls and Alkynes by Chiral Primary Amine/Rh Synergistic Catalysis

et al. 2022

Self Cite

View full text Add to dashboard Cite

show abstract

mentioning

confidence: 99%

“…On the basis of literature precedent, − ,,, we proposed a catalytic cycle for the current synergistic catalysis (Scheme ). The reaction is initialized by Rh(III)–H addition to alkyne 2a forming Rh-vinyl intermediate( I ), and subsequent β-hydride elimination leads to allene ( II ) and regenerates the Rh(III)–H species.…”

mentioning

confidence: 99%

Asymmetric Coupling of β-Ketocarbonyls and Alkynes by Chiral Primary Amine/Rh Synergistic Catalysis

et al. 2022

Self Cite

View full text Add to dashboard Cite

show abstract

“…In 2021, the same group, inspired by the early developments from Hartwig et al., [39] established a procedure for the functionalization of 28 with butadiene derivatives 78 (Scheme 18c) [40] . From a mechanistic standpoint, the addition to such chemical synthon proceeds as well to form π‐allyl intermediate, in presence of chiral amine 31 and Pd(OAc) 2 .…”

Section: Amino‐metal Synergistic Catalysismentioning

confidence: 99%

Synergistic Strategies in Aminocatalysis

Vecchio

Sinibaldi

Nori

et al. 2022

Chemistry A European J

View full text Add to dashboard Cite

Synergistic catalysis offers the unique possibility of simultaneous activation of both the nucleophile and the electrophile in a reaction. A requirement for this strategy is the stability of the active species towards the reaction conditions and the two concerted catalytic cycles. Since the beginning of the century, aminocatalysis has been established as a platform for the stereoselective activation of carbonyl compounds through HOMO-raising or LUMO-lowering. The burgeoning era of aminocatalysis has been driven by a deep understanding of these activation and stereoinduction modes, thanks to the introduction of versatile and privileged chiral amines. The aim of this review is to cover recent developments in synergistic strategies involving aminocatalysis in combination with organo-, metal-, photo-, and electrocatalysis, focusing on the evolution of privileged aminocatalysts architectures.

show abstract

“…This chiral primary amine/Pd synergistic catalyst system was later extended to the enamine coupling with allenes, vinylethylene carbonates and butadiene. [ 33,38,63 ] A chiral primary amine/Rh dual catalysis was also developed for the coupling of enamine with alkyne toward the construction of all‐carbon quaternary stereocenter. [ 64 ]…”

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

confidence: 99%

Bio‐inspired Small Molecular Catalysis

2022

Self Cite

View full text Add to dashboard Cite

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.

show abstract

Catalytic Asymmetric Addition and Telomerization of Butadiene with Enamine Intermediates

Cited by 15 publications

References 58 publications

Asymmetric Coupling of β-Ketocarbonyls and Alkynes by Chiral Primary Amine/Rh Synergistic Catalysis

Asymmetric Coupling of β-Ketocarbonyls and Alkynes by Chiral Primary Amine/Rh Synergistic Catalysis

Synergistic Strategies in Aminocatalysis

Bio‐inspired Small Molecular Catalysis

Contact Info

Product

Resources

About