One-Pot Synthesis of Chiral <i>Spiro</i>-Imidazolidinone Cyclohexenones

We have developed a simple and straightforward synthesis of chiral <i>spiro</i>-imidazolidinone cyclohexenones, featuring six contiguous stereocenters, from feedstock chemicals such as aminophenols, α,β-unsaturated aldehydes, and α-amino acids. Remarkably, this one-pot multicomponent reaction exhibits exceptional diastereoselectivity (>20:1 dr) and relies solely on an amino acid precursor as the chiral source, avoiding the use of transition metals or additional organocatalysts. This reaction is efficient and scalable, enabling synthesis on a gram-scale.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-12-23
DOI
https://doi.org/10.1021/acs.joc.4c02459
Citations
1
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
Field-Weighted Citation Impact
0.25

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article

One-Pot Synthesis of Chiral Spiro-Imidazolidinone Cyclohexenones

T. Dung
1 citations
The Journal of Organic Chemistry
Asymmetric Synthesis and Catalysis
0.25
article

One-Pot Synthesis of Chiral Spiro-Imidazolidinone Cyclohexenones

T. Dung
article en
1 citations

Abstract

We have developed a simple and straightforward synthesis of chiral <i>spiro</i>-imidazolidinone cyclohexenones, featuring six contiguous stereocenters, from feedstock chemicals such as aminophenols, α,β-unsaturated aldehydes, and α-amino acids. Remarkably, this one-pot multicomponent reaction exhibits exceptional diastereoselectivity (>20:1 dr) and relies solely on an amino acid precursor as the chiral source, avoiding the use of transition metals or additional organocatalysts. This reaction is efficient and scalable, enabling synthesis on a gram-scale.

The Journal of Organic ChemistryVol. 90(1)
Citadel (US)
Citadel Foundation
Openalex Percentile: Top 45%
Asymmetric Synthesis and Catalysis
0.25
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