(<i>Z</i>)-selective methoxy group-embedded Weinreb amide-type Horner–Wadsworth–Emmons reaction promoted by magnesium cation

Abstract Herein, a methoxy group-embedded Weinreb amide-type Horner–Wadsworth–Emmons reaction was developed for providing the functionally rich α,β-unsaturated carbonyl compounds. This reaction, promoted by magnesium cation, afforded the corresponding (Z)-alkenes from various substrates—including aliphatic and aromatic aldehydes—in high yields with satisfactory stereoselectivity. The elongated products, formed using the newly designed reagent, were easily converted into an α,β-unsaturated ketone, an α-keto-Weinreb amide, and further elongated compounds.

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Publication Details

Journal
Chemistry Letters
Published
2025-06-24
DOI
https://doi.org/10.1093/chemle/upaf119
Primary Topic
Phosphorus compounds and reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

(Z)-selective methoxy group-embedded Weinreb amide-type Horner–Wadsworth–Emmons reaction promoted by magnesium cation

Isamu Shiina, Hisazumi Tsutsui, Takatsugu Murata, Daiki Usukura
Chemistry Letters
Phosphorus compounds and reactions
article

(Z)-selective methoxy group-embedded Weinreb amide-type Horner–Wadsworth–Emmons reaction promoted by magnesium cation

Isamu Shiina, Hisazumi Tsutsui, Takatsugu Murata, Daiki Usukura
article en

Abstract

Abstract Herein, a methoxy group-embedded Weinreb amide-type Horner–Wadsworth–Emmons reaction was developed for providing the functionally rich α,β-unsaturated carbonyl compounds. This reaction, promoted by magnesium cation, afforded the corresponding (Z)-alkenes from various substrates—including aliphatic and aromatic aldehydes—in high yields with satisfactory stereoselectivity. The elongated products, formed using the newly designed reagent, were easily converted into an α,β-unsaturated ketone, an α-keto-Weinreb amide, and further elongated compounds.

Chemistry LettersVol. 54(7)
Tokyo University of Science (JP)
Suntory Foundation for Life Sciences
Openalex Percentile: Top 89%
Phosphorus compounds and reactions
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