Chiral Phosphine Catalyzed Allylic Alkylation of Benzylidene Succinimides with Morita-Baylis-Hillman Carbonates.

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Article in Molecules (Basel, Switzerland), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it

0cells of the map it votes in

1citing papers in PubMed

0.7field-weighted citation impact, top 35% of its field

1 · What the graph read from it

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Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

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3 · Its place in the literature

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1 citing paper in PubMed, 5 citations in OpenAlex.

Comparison of the Metabolomics of DifferentInternational journal of molecular sciences · 2023
Article

4 · The record

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5 · Who and what money

Authors and funding

3 authors at 2 institutions in 2 countries.

Chang LiuShenzhen Grubbs Institute, Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, College of Science, Southern University of Science and Technology (SUSTech), Shenzhen 518055, China.

Jianwei SunDepartment of Chemistry, The Hong Kong University of Science and Technology, Clear Water Bay, Kowloon, Hong Kong SAR, China.ORCID 0000-0002-2470-1077

Pengfei LiShenzhen Grubbs Institute, Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, College of Science, Southern University of Science and Technology (SUSTech), Shenzhen 518055, China.ORCID 0000-0001-5836-1069

Hong Kong University of Science and Technology · HKSouthern University of Science and Technology · CN

Funding

Guangdong Innovative Program 2019BT02Y335National Natural Science Foundation of China 21871128

6 · The paper itself

Abstract

Owing to their unique chemical properties, α-alkylidene succinimides generally act as versatile synthons in organic synthesis. Compared with well-established annulations, nucleophilic alkylations of α-alkylidene succinimides are very limited. Accordingly, an organocatalytic allylic alkylation of α-benzylidene succinimides with Morita-Baylis-Hillman (MBH) carbonates was established. In the presence of a chiral phosphine catalyst, α-benzylidene succinimides reacted smoothly with MBH carbonates under mild conditions to furnish a series of optical active succinimides in high yields and enantioselectivities. Different from the reported results, the organocatalytic enantioselective construction of pyrrolidine-2,5-dione frameworks bearing contiguous chiral tertiary carbon centers was achieved via this synthetic strategy. Scaling up the reaction indicated that it is a practical strategy for the organocatalytic enantioselective alkylation of α-alkylidene succinimides. A possible reaction mechanism was also proposed.

Indexed as

alkylationmaleimideMBH carbonatephosphinesuccinimide

Identifiers

PMID36985797

DOI10.3390/molecules28062825

PMCPMC10053092

OpenAlexW4328126393

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LicenceCC BY

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.