Asymmetric Michael/cyclization tandem reaction of 4-hydroxycoumarin with β-nitroalkenes catalyzed by chiral bifunctional thioureas

Mei, Ren‐Qiang; Xu, Xiao‐Ying; Peng, Lin; Wang, Fan; Tian, Fang; Wang, Lixin

doi:10.1039/c2ob27121d

Cited by 26 publications

(11 citation statements)

References 52 publications

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“…Wang and co‐workers treated nitroalkenes 76 and 4‐hydroxycoumarin ( 462 ) with a chiral bifunctional thiourea catalyst 464 and realized an asymmetric synthesis of 2,3‐dihydrofuro[3,2‐ c ]coumarin derivatives containing an exocyclic N ‐hydroxylimine group ( 463 ) in good yields and ee values via a domino Michael/cyclization reaction (Scheme ) …”

Section: Multifunctional Catalystsmentioning

confidence: 99%

Recent Progress in Organocatalytic Asymmetric Domino Transformations

2017

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Sustainability in chemical synthesis is a major aspect of the current synthetic endeavors and, therefore,m imicking the biological process in the laboratory nowadays has the highest priority.T owards achieving this goal, designingorganic reactions in domino mode rathert han the multistep synthetic pathways andu sing organocatalysisi nstead of metal catalysis have received al ot of attention due to the inherenta dvantageso ft hese processes in terms of synthetic efficiencya nd sustainability.A saresult, the field of asymmetric organocatalytic domino reactions has witnessed tremendous progress in recent years.T his review attempts to summarize the latest developments in asymmetric organocatalyzed domino reactions since 2012, with the emphasis on the catalysts andr eactionm odes.D iscussions on the reactionm echanismsa nd the applications of the developed domino reactionm ethodsi nt he synthesis of biologically active molecules and natural products are also includedwhen appropriate.

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Section: Multifunctional Catalystsmentioning

confidence: 99%

Recent Progress in Organocatalytic Asymmetric Domino Transformations

2017

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“…In turn, primary amines of this kind (Figure 12) were found most efficient in asymmetric additions to unsaturated ketones [180,181] and a stereoselective construction of α,α-disubstituted cycloalkanones [182]. A catalyst bearing two 1,2-diphenylethylenediamine fragments (Figure 12) was used in a tandem asymmetric Michael/cyclization reaction of 4-hydroxycoumarin and nitroalkanes, albeit with moderate yields [183]. 1,2-Dinaphthylethylenediamine derivatives were applied by Tius and co-workers in asymmetric Nazorov cyclization of diketones (Figure 13) [184,185].…”

Section: Thioureas Containing Trans-12-diaminocyclohexane (Dach) Skeleton and Other Chiral Diaminesmentioning

confidence: 99%

Chiral Thioureas—Preparation and Significance in Asymmetric Synthesis and Medicinal Chemistry

et al. 2020

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For almost 20 years, thioureas have been experiencing a renaissance of interest with the emerged development of asymmetric organocatalysts. Due to their relatively high acidity and strong hydrogen bond donor capability, they differ significantly from ureas and offer, appropriately modified, great potential as organocatalysts, chelators, drug candidates, etc. The review focuses on the family of chiral thioureas, presenting an overview of the current state of knowledge on their synthesis and selected applications in stereoselective synthesis and drug development.

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“…In 2013, Wang and co-workers described the first example of the organocatalytic asymmetric Michael/cyclization tandem reaction of 4-hydroxycoumarin with nitroalkenes. 71…”

Section: Cyclizations and Cycloadditionsmentioning

confidence: 99%