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

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

Publication Details

Journal
Figshare
Published
2024-12-23
DOI
https://doi.org/10.1021/acs.joc.4c02459.s001
Primary Topic
Synthesis of heterocyclic compounds
Type
article
Field-Weighted Citation Impact
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article

One-Pot Synthesis\nof Chiral Spiro-Imidazolidinone Cyclohexenones

Figshare
Synthesis of heterocyclic compounds
article

One-Pot Synthesis\nof Chiral Spiro-Imidazolidinone Cyclohexenones

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Abstract

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

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Openalex Percentile: Top 80%
Synthesis of heterocyclic compounds
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One-Pot Synthesis\nof Chiral <i>Spiro</i>-Imidazolidinone Cyclohexenones · Figshare (2024) | TGRS Research Map | TGRS