Asymmetric Synthesis of Either Enantiomer of β-Butadienyl Amines by Isoprenylation of Davis–Ellman Imines

The asymmetric synthesis of either enantiomer of β-butadienyl amines from a single starting material is described. Reversal of the diastereoselectivity is achieved by simply tuning the reaction conditions. This methodology provides excellent yields (up to 98%) and high diastereomeric ratios (<i>dr</i> up to 98:2) and exhibits a broad substrate scope.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-06-07
DOI
https://doi.org/10.1021/acs.joc.5c00463
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
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article

Asymmetric Synthesis of Either Enantiomer of β-Butadienyl Amines by Isoprenylation of Davis–Ellman Imines

Leleti Rajender Reddy, Shiva Kumar Koppula, Venu Aili
The Journal of Organic Chemistry
Asymmetric Synthesis and Catalysis
article

Asymmetric Synthesis of Either Enantiomer of β-Butadienyl Amines by Isoprenylation of Davis–Ellman Imines

Leleti Rajender Reddy, Shiva Kumar Koppula, Venu Aili
article en

Abstract

The asymmetric synthesis of either enantiomer of β-butadienyl amines from a single starting material is described. Reversal of the diastereoselectivity is achieved by simply tuning the reaction conditions. This methodology provides excellent yields (up to 98%) and high diastereomeric ratios (<i>dr</i> up to 98:2) and exhibits a broad substrate scope.

The Journal of Organic ChemistryVol. 90(24)
GITAM University (IN)
Openalex Percentile: Top 90%
Asymmetric Synthesis and Catalysis
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