Asymmetric synthesis of 1H-pyrrol-3(2H)-ones from 2,3-diketoesters by combination of aldol condensation with benzilic acid rearrangement

Sha, Qiang; Arman, Hadi D.; Doyle, Michael P.

doi:10.1039/c5cc07780j

Cited by 33 publications

(15 citation statements)

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“…The most recent application of vic-tricarbonyl compounds in the stereocontrolled synthesis of heterocycles is a proline-catalysed synthesis of 1H-pyrrol-3(2H)-ones 65 starting from vic-diketo esters 55 and cyclohexanone (58). 32 As shown in Scheme 14, the reaction provides excellent enantioselectivities regardless of the employed amine or ester. In the case of aliphatic amines, however, only moderate yields could be obtained.…”

Section: Short Review Syn Thesismentioning

confidence: 98%

Vicinal Tricarbonyl Compounds: Versatile Building Blocks for Natural Product Synthesis

et al. 2016

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Due to their high density of functional groups, vicinal tricarbonyl compounds are versatile building blocks for the synthesis of complex target molecules. Methods for their preparation and their use in stereoselective CC bond formations, as well as for the synthesis of heteroaromatics, are summarised for the period 2006-2016. Several examples for their applications in natural product synthesis (awajanomycin, cladoniamide, wailupemycin) are presented. 1 Introduction 2 Preparation of Vicinal Tricarbonyl Compounds 3 Use in Stereoselective CC Bond Formations 4 Use for the Synthesis of Heteroaromatics 5 Examples from Natural Product Synthesis 6 Conclusion Key words vicinal tricarbonyl compounds, stereoselective synthesis, natural products, total synthesis, regioselectivity Lars Selter (from left to right) was born in Berlin, Germany in 1989. He studied chemistry at the Freie Universität Berlin and received his B.Sc. degree in 2011 and his M.Sc. degree in 2013 under the supervision of Prof. H.-U. Reißig. Currently, he is working as a Ph.D. student at the Philipps-Universität Marburg under the guidance of Prof. U. Koert focusing on regioselective CC bond formation on vicinal tricarbonyl compounds. Lukas Zygalski was born in Rotenburg/Fulda, Germany in 1990. He completed his B.Sc. degree in 2013 and his M.Sc. degree (specialisation in organic chemistry) in 2016 under the supervision of Prof. U. Koert at the Philipps-Universität Marburg. Currently, he is working there as a Ph.D. student focusing on natural product synthesis. Eric Kerste was born in Rotenburg/Fulda, Germany in 1990. He completed his B.Sc. degree in 2013 and his M.Sc. degree (specialisation in organic chemistry) in 2016, both under the supervision of Prof. U. Koert at the Philipps-Universität Marburg. Currently, he is working there as a Ph.D. student focusing on natural product synthesis based on vicinal diketo esters. Ulrich Koert was born in Hanau, Germany in 1961. He studied chemistry at the Goethe Universität in Frankfurt where he obtained his Ph.D. in

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Section: Short Review Syn Thesismentioning

confidence: 98%

Vicinal Tricarbonyl Compounds: Versatile Building Blocks for Natural Product Synthesis

et al. 2016

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“…The major diastereoisomers 107 are explored in benzilic acid rearrangement using different variants of amines in the presence of trifluoroacetic acid as an additive (65 C; 24 hours) to yield condensed pyrrolin-3-ones 108 (87%; 99% ee) (Scheme 42). 30 Various halogen substituted aniline (-F, -Cl, -Br, -I), or anilines with either electron donating groups (−Me, -OMe) or electron-withdrawing groups (-CN, -NO 2 ) provide 1H-pyrrol-3(2H)-ones 108 in high yield (99% ee). Aliphatic amines such as hexadecylamine afford 108 in moderate yields (46%; 99% ee) (Scheme 43).…”

Section: Synthesis Of 1h-pyrrol-3 (2h)-ones From Diketonesmentioning

confidence: 99%

“…The major diastereoisomers 107 are explored in benzilic acid rearrangement using different variants of amines in the presence of trifluoroacetic acid as an additive (65°C; 24 hours) to yield condensed pyrrolin‐3‐ones 108 (87%; 99% ee) (Scheme 42). 30 …”

Section: Synthesis Of 1h‐pyrrol‐3(2h)‐ones From Diketonesmentioning

confidence: 99%

Recent development in the synthesis of pyrrolin‐4‐ones/pyrrolin‐3‐ones

Sharma

Kumar

Bhargava

2020

Journal of Heterocyclic Chem

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Pyrrolin-4-ones/pyrrolin-3-ones and its derivatives are important heterocyclic systems which are observed in vast variety of natural products, pharmaceuticals, and biologically important compounds. Different researchers all across the world have developed different synthetic methodologies for the construction of functionalized pyrrolin-4-ones/pyrrolin-3-one scaffolds such as the transition-metal catalyzed/mediated cycloisomerizations of 1-aminoynones and dimerization of enaminones or α-diazo-β-oxoamides etc. The present review article summarizes various reports on the synthesis of various simple and functionalized pyrrolin-4-ones/pyrrolin-3-ones from 2000 onward.

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“…Due to the easy accessibility of 2,3‐diketoesters [9] and cyclohexanones, a variety of 2‐hydroxy‐1,4‐dione derivatives could be readily obtained. Subsequently, we applied these novel 2‐hydroxy‐1,4‐diones to the synthesis of 2‐vinylpyrroles, [10] pyrrol‐3‐ones, [8a] and benzofurans [11] . Carbocation [12] intermediates are involved in these transformations, which allows the subsequent cascade reactions to occur smoothly.…”

Section: Introductionmentioning

confidence: 99%

De Novo and Divergent Synthesis of Highly Functionalized Furans by Cascade Reactions of 2‐Hydroxy‐1,4‐diones with Nucleophiles

Liu

Chen

et al. 2021

Chemistry A European J

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Herein, a divergent synthesis of a variety of 2α‐ and 5α‐substituted furan derivatives from 2‐hydroxy‐1,4‐diones is reported. By using appropriate substrates and an acid catalyst, the reactions occurred selectively through cyclization/1,6‐conjugate addition or cyclization/Friedel–Crafts‐type cascade reactions. A broad range of nucleophilic reagents (>10 types for the 1,6‐conjugate addition for 5α substitution and >20 types for the Friedel–Crafts‐type cascade reaction for 2α substitution), including alcohols, amides, furan, thiophene, pyrrole, indole, phenols, and many others, can successfully participate in the reactions, providing a universal strategy for a diversity‐oriented synthesis of α‐substituted furan derivatives. Deuteriation experiments and DFT calculations were carried out to support the proposed reaction mechanisms. Antifungal activity experiments revealed that products with an indole or 4‐hydroxycoumarin core substituted at the 2α position showed moderate activities against Rhizoctorzia solani and Botrytis cinerea, respectively.

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Asymmetric synthesis of 1H-pyrrol-3(2H)-ones from 2,3-diketoesters by combination of aldol condensation with benzilic acid rearrangement

Abstract: An efficient two-step protocol for the asymmetric synthesis of 1H-pyrrol-3(2H)-one derivatives in 99% ee from conveniently accessed 2, 3-diketoesters has been developed.

Cited by 33 publications

References 61 publications

Vicinal Tricarbonyl Compounds: Versatile Building Blocks for Natural Product Synthesis

Vicinal Tricarbonyl Compounds: Versatile Building Blocks for Natural Product Synthesis

Recent development in the synthesis of pyrrolin‐4‐ones/pyrrolin‐3‐ones

De Novo and Divergent Synthesis of Highly Functionalized Furans by Cascade Reactions of 2‐Hydroxy‐1,4‐diones with Nucleophiles

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