Enantioselective Sulfonation of Enones with Sulfonyl Imines by Cooperative N‐Heterocyclic‐Carbene/Thiourea/Tertiary‐Amine Multicatalysis

Jin, Zhichao; Xu, Jianfeng; Yang, Song; Song, Baoan; Robin, Yonggui

doi:10.1002/ange.201305023

Cited by 89 publications

(11 citation statements)

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“…These results suggest that non-covalent interaction is likely to play an important role in controlling the enantioselectivity of our reactions. We thus examined non-covalent organic catalysts and found that using achiral thiourea3738394041 A1 as a co-catalyst could improve the e.r. values of 3a from 73:27 to 85:15 (entry 6 versus 4).…”

Section: Resultsmentioning

confidence: 99%

A reaction mode of carbene-catalysed aryl aldehyde activation and induced phenol OH functionalization

et al. 2017

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The research in the field of asymmetric carbene organic catalysis has primarily focused on the activation of carbon atoms in non-aromatic scaffolds. Here we report a reaction mode of carbene catalysis that allows for aromatic aldehyde activation and remote oxygen atom functionalization. The addition of a carbene catalyst to the aldehyde moiety of 2-hydroxyl aryl aldehyde eventually enables dearomatization and remote OH activation. The catalytic process generates a type of carbene-derived intermediate with an oxygen atom as the reactive centre. Inexpensive achiral urea co-catalyst works cooperatively with the carbene catalyst, leading to consistent enhancement of the reaction enantioselectivity. Given the wide presence of aromatic moieties and heteroatoms in natural products and synthetic functional molecules, we expect our reaction mode to significantly expand the power of carbene catalysis in asymmetric chemical synthesis.

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Section: Resultsmentioning

confidence: 99%

A reaction mode of carbene-catalysed aryl aldehyde activation and induced phenol OH functionalization

et al. 2017

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“…The elegant strategy of NHC/bifunctional H‐bonding catalysis [54] was exhibited by Chi and coworkers, which was employed to perform an asymmetric sulfonation of sulfonylimines 93 with enones 94 (Scheme 30). [55] With the different combination of catalyst, the enone possessing aryl and alkyl group substituted at the β ‐position could be well compatible under the enantioselective conditions to afford product 95 or 96 . In this process, the NHC catalyst serves as an activator to cleave the N−S bond of sulfonylimine 93 , and leads to generation of a sulfinic anion nucleophile.…”

Section: Asymmetric Reactions Catalyzed By Multi‐organocatalystsmentioning

confidence: 99%

Recent Advances in Asymmetric Organomulticatalysis

Xiao

Shao

et al. 2020

Adv Synth Catal

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Asymmetric multi‐catalysis, designed to mimic catalytic processes in nature, is a powerful instrument to fulfil fascinating transformations. As a result, this area of research has attracted considerable interests within chemistry communities. Although there are numerous reviews involving multi‐catalysis, reviews describing asymmetric organomulticatalysis remain rare. Taking into consideration that organocatalysts possess the superiorities of effortless availability, inexpensiveness, hypotoxicity, facile handling and hyposensitivity to moisture and oxygen, they have definite advantage in their own distinct modes of activation when utilized in multi‐catalytic reactions. Organomulticatalysis refers to the synthetic strategies of modular combination of organo‐catalyzed reactions into one synthetic operation with minimum workup or change in conditions. It is apparent that a variety reports utilizing the concept of enantioselective organomulticatalysis have substantially surfaced in the past few years. Hence, it is indispensable to succinctly present all such reports by means of disclosing the mechanistic analysis, as well as the challenges and issues associated in the development of the asymmetric catalytic system. Additionally, this review will introduce some of the unsettled conundrums and possible innovations in this field.

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“…The Singapore Young Scientist Award, which is part of the President’s Science and Technology Awards, is administered by the Singapore National Academy of Sciences and supported by A*STAR (Agency of Science, Technology and Research), and is presented to researchers under the age of 35 years. Among the award winners were Qui Cheng Wei (National University of Singapore) and Yonggui Robin Chi (Nanyang Technical University; NTU), who has reported in Angewandte Chemie on N‐heterocyclic carbene organocatalysis,2a and on the use of multicatalysis in the enantioselective sulfonation of enones 2b. Chi studied at Hong Kong Baptist University and Tsinghua University, and carried out his PhD (awarded in 2007) under the supervision of Samuel H. Gellman at the University of Wisconsin–Madison.…”

Section: Awarded …︁mentioning

confidence: 99%

Otto Hahn Prize: F. Krausz / DECHEMA Prize: T. Scheibel / Singapore Young Scientist Award: Y. R. Chi / Science Award Electrochemistry: K. J. J. Mayrhofer / President of the Gesellschaft Deutscher Chemiker: T. Geelhaar / Eric and Sheila Samson Prime Minister's Prize for Innovation in Alternative Fuels for Transportation: G. A. Olah und G. K. S. Prakash / TEVA Award for Excellence: A. Brik und D. S. Tawfik / Marcel Benoist Prize: M. Grätzel / Meienhofer Award: H. Kessler

2013

Angew Chem Int Ed

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Enantioselective Sulfonation of Enones with Sulfonyl Imines by Cooperative N‐Heterocyclic‐Carbene/Thiourea/Tertiary‐Amine Multicatalysis

Abstract: Scheme 1. Enantioselective catalytic sulfonation of enones. Tol = p-tolyl.

Cited by 89 publications

References 83 publications

A reaction mode of carbene-catalysed aryl aldehyde activation and induced phenol OH functionalization

A reaction mode of carbene-catalysed aryl aldehyde activation and induced phenol OH functionalization

Recent Advances in Asymmetric Organomulticatalysis

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