<scp>l</scp>-Amino acid ester as a biomimetic reducing agent for the reduction of unsaturated CC bonds

The first example of an efficient protocol for the reduction of disubstituted methyleneindolinones, isoindigos and tetrasubstituted olefins for the synthesis of 3-substituted 2-oxindoles, dihydroisoindigos and tetrasubstituted ethane derivatives using an L-amino acid ester as an attractive biomimetic reducing agent has been developed. This new protocol has the advantages of mild reaction conditions without the need for any metal catalysts, a broad substrate scope (31 examples), excellent yields (90-98%) and good functional group tolerance, providing an operationally simple and practically useful methodology for reductive reactions. The L-amino acid derivative, which is cheap, nontoxic and easy to handle, serves as a new biomimetic reducing agent for use in organic chemistry, providing a novel and promising approach for future applications in reductive reactions.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2024-11-19
DOI
https://doi.org/10.1039/d4ob01640h
Citations
2
Primary Topic
thermodynamics and calorimetric analyses
Type
article
Field-Weighted Citation Impact
0.89
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article

l-Amino acid ester as a biomimetic reducing agent for the reduction of unsaturated CC bonds

Yinfeng Han, Yabin Wang, H.-T. Shi, Ji‐Wei Ren et al.
2 citations
Organic & Biomolecular Chemistry
thermodynamics and calorimetric analyses
0.89
article

l-Amino acid ester as a biomimetic reducing agent for the reduction of unsaturated CC bonds

Yinfeng Han, Yabin Wang, H.-T. Shi, Ji‐Wei Ren, Jing-Hui Sun, Huai-Xin Zhang, Cheng-Shuai Han, Qing-Hao Zhang
article en
2 citations

Abstract

The first example of an efficient protocol for the reduction of disubstituted methyleneindolinones, isoindigos and tetrasubstituted olefins for the synthesis of 3-substituted 2-oxindoles, dihydroisoindigos and tetrasubstituted ethane derivatives using an L-amino acid ester as an attractive biomimetic reducing agent has been developed. This new protocol has the advantages of mild reaction conditions without the need for any metal catalysts, a broad substrate scope (31 examples), excellent yields (90-98%) and good functional group tolerance, providing an operationally simple and practically useful methodology for reductive reactions. The L-amino acid derivative, which is cheap, nontoxic and easy to handle, serves as a new biomimetic reducing agent for use in organic chemistry, providing a novel and promising approach for future applications in reductive reactions.

Organic & Biomolecular ChemistryVol. 23(3)
Taishan University (CN)
Openalex Percentile: Top 20%
thermodynamics and calorimetric analyses
0.89
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<scp>l</scp>-Amino acid ester as a biomimetic reducing agent for the reduction of unsaturated CC bonds — Yinfeng Han, Yabin Wang, et al. · Organic & Biomolecular Chemistry (2024) | TGRS Research Map | TGRS