DFT Insights into NHC-Catalyzed Switchable [3+4] and [3+2] Annulations of Isatin-Derived Enals and N-Sulfonyl Ketimines: Mechanism, Regio- and Stereoselectivity.

Saisai Yu, Wenxin Zhou, Yueming Jiang, Hangyu Wang, Xiaoyu Zhou, Shengwen Yang

Abstract read

In one paragraph

Article in Molecules (Basel, Switzerland), 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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5 · Who and what money

Authors and funding

6 authors.

Saisai YuKey Laboratory of Xinjiang Endemic Phytomedicine Resources, Ministry of Education, School of Pharmacy, Shihezi University, Shihezi 832002, China.

Wenxin ZhouKey Laboratory of Xinjiang Endemic Phytomedicine Resources, Ministry of Education, School of Pharmacy, Shihezi University, Shihezi 832002, China.

Yueming JiangKey Laboratory of Xinjiang Endemic Phytomedicine Resources, Ministry of Education, School of Pharmacy, Shihezi University, Shihezi 832002, China.

Hangyu WangKey Laboratory of Xinjiang Endemic Phytomedicine Resources, Ministry of Education, School of Pharmacy, Shihezi University, Shihezi 832002, China.

Xiaoyu ZhouSchool of Pharmaceutical and Chemical Engineering, Taizhou University, Taizhou 317700, China.

Shengwen YangKey Laboratory of Xinjiang Endemic Phytomedicine Resources, Ministry of Education, School of Pharmacy, Shihezi University, Shihezi 832002, China.ORCID 0000-0001-9449-3077

Funding

Shihezi University Interdisciplinary Research Program (JCYJ202310)，Yunnan Key Laboratory of Chiral Functional Substance Research and Application (202402AN360010) JCYJ202310，202402AN360010

6 · The paper itself

Abstract

Density functional theory (DFT) calculations at the M06-2X-D3/6-311++G(2df,2pd) level elucidate the mechanism and selectivity origins in the NHC-catalyzed divergent synthesis of spirocyclopentane oxindoles from isatin-derived enals and N-sulfonyl ketimines. The Michael addition constitutes the regio- and stereoselectivity-determining step, where Parr function analysis demonstrates that nucleophile/electrophile electrophilicity governs regioselectivity, while distortion/interaction and non-covalent interaction analyses reveal stereoselectivity is controlled by distortion and weak interactions. K

Indexed as

[3+2] annulation[3+4] annulationisatin-derived enalN-heterocyclic carbenespirocyclopentane oxindole

Identifiers

PMID41226179

DOI10.3390/molecules30214218

PMCPMC12609633

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