Recent advances in the synthetic applications of Morita–Baylis–Hillman and Rauhut–Currier adducts of nitroalkenes

Namboothiri, Irishi N. N.; Sivanandan, Sudheesh T.; Nair, Divya K

doi:10.1039/d3ob00853c

Cited by 4 publications

(1 citation statement)

References 90 publications

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“…Nitroalkenes were identied as efficient substrates in the MBH reaction. 57 It is possible to perform the MBH reaction on b-aminonitroalkenes without the need of a base or catalyst. 58 b-Aminonitroalkene was treated with various electrophiles, including ninhydrin, vinyl sulphone, triuropyrate, ethyl glyoxylate, and N-tosylazadienes in acetonitrile at room temperature (Scheme 40).…”

Section: Miscellaneousmentioning

confidence: 99%

Recent progress and prospects in the organocatalytic Morita–Baylis–Hillman reaction

Maneesha,

Haritha,

Aneeja

et al. 2024

RSC Adv.

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Section: Miscellaneousmentioning

confidence: 99%

Recent progress and prospects in the organocatalytic Morita–Baylis–Hillman reaction

Maneesha,

Haritha,

Aneeja

et al. 2024

RSC Adv.

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Metal‐Free [2+3] Dipolar Cycloaddition/Denitration Cascade between Nitroalkenes and α‐Diazoesters: Regioselective Access to Functionalized NH−Pyrazoles

Kumar,

Ray,

Saha

et al. 2024

Asian J Org Chem

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An efficient one‐pot synthesis of 1H‐pyrazoles has been realized via cascade cyclocondensation of β‐nitroalkenes as C2 synthon with α‐diazoesters as C1N2 unit. The reaction proceeds via concomitant formation of two new (C‐N & C‐C) bonds in one stretch leading to ethyl 5‐nitro‐4‐phenyl‐4,5‐dihydro‐3H‐pyrazole‐3‐carboxylate intermediate, which undergoes base mediated denitration enabling the formation of NH‐pyrazoles. This protocol not only features easy operation, catalyst‐free conditions, good to high yields, wide scope and late‐stage functionalization, but also opens up a new avenue for synthetically demanding and structurally non‐traditional pyrazoles. A combination of experimental and DFT studies provide evidence for the proposed mechanism.

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Stereocontrolled Construction of Spirooxindole-Containing 5,6,7,8-Tetrahydropyrrolo[1,2-a]pyridine via Michael/Friedel–Crafts Domino Reaction Promoted by Secondary Amine-Squaramide

Yin,

Zhou,

Shi

et al. 2024

Org. Lett.

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An asymmetric Michael/Friedel−Crafts cascade reaction with Morita−Baylis−Hillman (MBH) nitroallylic esters and 3-pyrrolyloxindoles has been developed for the stereoselective construction of spirooxindole-containing tetrahydroindolizines. A range of tetracyclic scaffolds possessing three consecutive chiral centers, including an all-carbon quaternary stereocenter, were generated in 53−85% isolated yields with high diastereoselectivities and enantiopurities (≥3:1 dr, 50−98% ee). A newly synthesized bifunctional secondary amine/squaramide organocatalyst was demonstrated to exhibit better stereochemical control than their tertiary analogues. 5,6,7,8-Tetrahydroindolizine represents a fascinating core structure widely embedded in several families of natural alkaloids, such as polygonatine, 1 myrmicarin, 2 rhazinilam, and lamellarin (Figure 1). In particular, all of these alkaloids are

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Recent advances in the synthetic applications of Morita–Baylis–Hillman and Rauhut–Currier adducts of nitroalkenes

Abstract: The Morita-Baylis-Hillman (MBH) and Rauhut-Currier (RC) adducts of nitroalkenes are important synthetic intermediates in organic synthesis. This review discusses the application of different MBH and RC adducts of nitroalkenes such...

Cited by 4 publications

References 90 publications

Recent progress and prospects in the organocatalytic Morita–Baylis–Hillman reaction

Recent progress and prospects in the organocatalytic Morita–Baylis–Hillman reaction

Metal‐Free [2+3] Dipolar Cycloaddition/Denitration Cascade between Nitroalkenes and α‐Diazoesters: Regioselective Access to Functionalized NH−Pyrazoles

Stereocontrolled Construction of Spirooxindole-Containing 5,6,7,8-Tetrahydropyrrolo[1,2-a]pyridine via Michael/Friedel–Crafts Domino Reaction Promoted by Secondary Amine-Squaramide

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