One-Pot Synthesis of Chiral Allenes Mediated by Decahydroquinoxaline Scaffolds

We report a direct and efficient one-pot strategy for the synthesis of highly enantioselective (<i>R</i>)-allenes using 1-alkynes and aromatic aldehydes mediated by decahydroquinoxaline scaffolds. The reaction, promoted by ZnI<sub>2</sub> in toluene at 120 °C, proceeds smoothly under mild conditions, affording chiral allenes with good yields (57-85% for aliphatic alkynes and 25% for the aromatic alkyne) and excellent enantioselectivities (83-96%) within 4 h. This method offers a straightforward and practical approach for constructing valuable chiral allene frameworks that are potentially useful in organic synthesis and medicinal chemistry. The use of decahydroquinoxaline scaffolds enables effective chirality transfer, making this protocol a promising tool for stereoselective transformation.

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Publication Details

Journal
ACS Omega
Published
2025-11-12
DOI
https://doi.org/10.1021/acsomega.5c04812
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

One-Pot Synthesis of Chiral Allenes Mediated by Decahydroquinoxaline Scaffolds

Laxman Mahadev Alakonda, Mariappan Periasamy
ACS Omega
Catalytic C–H Functionalization Methods
article

One-Pot Synthesis of Chiral Allenes Mediated by Decahydroquinoxaline Scaffolds

Laxman Mahadev Alakonda, Mariappan Periasamy
article en

Abstract

We report a direct and efficient one-pot strategy for the synthesis of highly enantioselective (<i>R</i>)-allenes using 1-alkynes and aromatic aldehydes mediated by decahydroquinoxaline scaffolds. The reaction, promoted by ZnI<sub>2</sub> in toluene at 120 °C, proceeds smoothly under mild conditions, affording chiral allenes with good yields (57-85% for aliphatic alkynes and 25% for the aromatic alkyne) and excellent enantioselectivities (83-96%) within 4 h. This method offers a straightforward and practical approach for constructing valuable chiral allene frameworks that are potentially useful in organic synthesis and medicinal chemistry. The use of decahydroquinoxaline scaffolds enables effective chirality transfer, making this protocol a promising tool for stereoselective transformation.

ACS OmegaVol. 10(46)
University of Wyoming (US), University of Hyderabad (IN), Wyoming Department of Education (US)
Openalex Percentile: Top 72%
Catalytic C–H Functionalization Methods
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