Enantioselective Allylic Amination of Morita‐Baylis‐Hillman Acetates Catalyzed by Chiral Thiourea‐Phosphine

Zhao, Xuan; Kang, Tian-Chen; Shen, Jie; Sha, Feng; Wu, Xin‐Yan

doi:10.1002/cjoc.201500697

Cited by 15 publications

(10 citation statements)

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“…In 2015, Wu, Sha, and co-workers synthesized and applied the chiral thiourea-phosphine P87 to the allylic amination of MBH acetates with phthalimide 593 but obtained only moderate to good enantioselectivities (Scheme 525).…”

Section: Nucleophilic Phosphine Catalysis Of Mbh-alcohol Derivatives mentioning

confidence: 99%

Phosphine Organocatalysis

et al. 2018

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The hallmark of nucleophilic phosphine catalysis is the initial nucleophilic addition of a phosphine to an electrophilic starting material, producing a reactive zwitterionic intermediate, generally under mild conditions. In this Review, we classify nucleophilic phosphine catalysis reactions in terms of their electrophilic components. In the majority of cases, these electrophiles possess carbon–carbon multiple bonds: alkenes (section 2), allenes (section 3), alkynes (section 4), and Morita–Baylis–Hillman (MBH) alcohol derivatives (MBHADs; section 5). Within each of these sections, the reactions are compiled based on the nature of the second starting material—nucleophiles, dinucleophiles, electrophiles, and electrophile–nucleophiles. Nucleophilic phosphine catalysis reactions that occur via the initial addition to starting materials that do not possess carbon–carbon multiple bonds are collated in section 6. Although not catalytic in the phosphine, the formation of ylides through the nucleophilic addition of phosphines to carbon–carbon multiple bond–containing compounds is intimately related to the catalysis and is discussed in section 7. Finally, section 8 compiles miscellaneous topics, including annulations of the Hüisgen zwitterion, phosphine-mediated reductions, iminophosphorane organocatalysis, and catalytic variants of classical phosphine oxide–generating reactions.

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Section: Nucleophilic Phosphine Catalysis Of Mbh-alcohol Derivatives mentioning

confidence: 99%

Phosphine Organocatalysis

et al. 2018

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“…Moreover, rosin-derived thioureas can be used as enantioselective catalysts for many reactions [12]. In recent years these were: Michael addition [223,224], tandem Michael/cyclization sequence [225], asymmetric Michael/hemiketalization [226], asymmetric aza-Henry reaction [227], asymmetric tandem reaction [228], Mannich reaction [229,230], Friedel–Crafts alkylation [231], enantio- and diastereoselective asymmetric addition [232], as well as synthesis of chiral amines [233] or N -protected β-amino malonates [234]. In recent studies rosin-derived thioureas are dominant majority of all investigated rosin-derived catalysts.…”

Section: Rosin-based Chemicalsmentioning

confidence: 99%

Advances in Rosin-Based Chemicals: The Latest Recipes, Applications and Future Trends

et al. 2019

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A comprehensive review of the publications about rosin-based chemicals has been compiled. Rosin, or colophony, is a natural, abundant, cheap and non-toxic raw material which can be easily modified to obtain numerous useful products, which makes it an excellent subject of innovative research, attracting growing interest in recent years. The last extensive review in this research area was published in 2008, so the current article contains the most promising, repeatable achievements in synthesis of rosin-derived chemicals, published in scientific literature from 2008 to 2018. The first part of the review includes low/medium molecule weight compounds: Especially intermediates, resins, monomers, curing agents, surfactants, medications and biocides. The second part is about macromolecules: mainly elastomers, polymers for biomedical applications, coatings, adhesives, surfactants, sorbents, organosilicons and polysaccharides. In conclusion, a critical evaluation of the publications in terms of data completeness has been carried out with an indication of the most promising directions of rosin-based chemicals development.

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“…In 2015, Sha and co‐workers found that the chiral cyclohexane‐based thiourea–phosphine 55 , derived from dehydroabietic acid, was able to catalyze the enantioselective allylic amination of phthalimide with MBH acetates (Scheme a) . Catalyst screening demonstrated that the matching effects between the cyclohexyl backbone and dehydroabietic unit were crucial to achieve a good level of enantioselectivity.…”

Section: Terpene‐derived Organocatalystsmentioning

confidence: 99%

“…In 2015, Sha and co-workers found that the chiral cyclohexane-based thiourea-phosphine 55,d erived from dehydroabietic acid, was able to catalyzet he enantioselectivea llylic amination of phthalimide with MBHa cetates (Scheme 37 a). [110] Cata-Scheme34. Asymmetric Michaela ddition for the synthesis of substituted succinimides promoted by an isosteviol-derived bifunctional thiourea organocatalyst.…”

Section: Rosin-derived Organocatalystsmentioning

confidence: 99%

“…In 2015, Sha and co-workers found that the chiral cyclohexane-based thiourea-phosphine 55,d erived from dehydroabietic acid, was able to catalyzet he enantioselectivea llylic amination of phthalimide with MBHa cetates (Scheme 37 a). [110] Cata-lyst screening demonstrated that the matching effects between the cyclohexylb ackbonea nd dehydroabietic unit were crucial to achieve ag ood level of enantioselectivity.I nt he presenceo f2 0mol % 55 and 20 mol %N Et 3 ,t he desired chiral amines 56 were produced in moderate to good yields and up to 85 % ee. Unfortunately,d ifferent N-nucleophiles, such as aniline, benzylamine, ands ulfonamide, were found to be unsuitable substrates.…”

Section: Rosin-derived Organocatalystsmentioning

confidence: 99%

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Valorization of Waste: Sustainable Organocatalysts from Renewable Resources

Meninno

2019

ChemSusChem

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443 Reviews Figure 2. Potential organocatalytic modes of activatione xhibited by chitosan.Scheme2.Monoglycerides ynthesis by ring opening of the glycidol catalyzed by chitosan. 444 ReviewsScheme3.Aldol reaction between 4-nitrobenzaldehyde (1)a nd cyclohexanone (2)promoted by chitosan hydrogel beads. Scheme4.Aldol reactionscatalyzed by dried chitosan gels and proposed catalytic modes of activation. 445 Reviews Scheme5.Aldol reaction in water promoted by chitosan aerogel beads (additivesu sed at 20 mol %: DNP = 2,4-dinitrophenol, SA = stearic acid, SDS = sodium dodecyl sulfate,B oc = tert-butyloxycarbonyl; ee = enantiomeric excess). Scheme6.Aldol reactionscatalyzedb yc hitosan in 1-butyl-3-methylimidazolium bromide ([bmim][Br])at3 78C. 446 Reviews Scheme16. Asymmetric aldol reaction in water catalyzedb yc hitosan-supported cinchonine. Scheme15. Chitosan-catalyzed transamidation of carboxamides with amines under neat conditions. 450 Reviews Scheme17. Knoevenagelcondensation of challenging aldehydes promoted by native and modified chitosan-derived hydrogels ([a] conversion valuesare reported). 458 Reviews Scheme33. Stereoselective Michael reaction catalyzedbyan aturalpinanederived bifunctional organocatalyst. Scheme32. Stereoselective Mannich reaction catalyzed by d-glucosamine-derived organocatalyst and the hypothetical reaction TS. 460 Reviews Scheme35. a) Synthesis of organocatalyst 52 derived from abietic acid. b) Asymmetric direct aldol reaction catalyzed by 52.c)Proposed TS model. 461 ReviewsScheme42. a) Reductive transformation of CO 2 with amines into formamidesand methylamines organocatalyzedbyl ecithin, and b) plausible reaction mechanism.

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Enantioselective Allylic Amination of Morita‐Baylis‐Hillman Acetates Catalyzed by Chiral Thiourea‐Phosphine

Cited by 15 publications

References 54 publications

Phosphine Organocatalysis

Phosphine Organocatalysis

Advances in Rosin-Based Chemicals: The Latest Recipes, Applications and Future Trends

Valorization of Waste: Sustainable Organocatalysts from Renewable Resources

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