Stereo- and Enantioselective Syntheses of (<i>Z</i>)-1,3-Butadienyl-2-carbinols via Brønsted Acid Catalysis

A Brønsted acid-catalyzed enantioselective synthesis of (<i>Z</i>)-1,3-butadienyl-2-carbinols is developed. By employing a chiral phosphoric acid as the catalyst, a variety of 1,3-butadienyl-2-carbinols were obtained in good yields with excellent <i>Z</i>-selectivities and enantiopurities from α-alkyl-substituted homoallenyl boronates.

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Publication Details

Journal
Organic Letters
Published
2025-01-09
DOI
https://doi.org/10.1021/acs.orglett.4c04663
Primary Topic
Asymmetric Synthesis and Catalysis
Type
article
Field-Weighted Citation Impact
0.00

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article

Stereo- and Enantioselective Syntheses of (Z)-1,3-Butadienyl-2-carbinols via Brønsted Acid Catalysis

Ming Chen
Organic Letters
Asymmetric Synthesis and Catalysis
article

Stereo- and Enantioselective Syntheses of (Z)-1,3-Butadienyl-2-carbinols via Brønsted Acid Catalysis

Ming Chen
article en

Abstract

A Brønsted acid-catalyzed enantioselective synthesis of (<i>Z</i>)-1,3-butadienyl-2-carbinols is developed. By employing a chiral phosphoric acid as the catalyst, a variety of 1,3-butadienyl-2-carbinols were obtained in good yields with excellent <i>Z</i>-selectivities and enantiopurities from α-alkyl-substituted homoallenyl boronates.

Organic LettersVol. 27(3)
Virginia Tech (US)
National Science Foundation, Division of Chemistry
Openalex Percentile: Top 100%
Asymmetric Synthesis and Catalysis
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Stereo- and Enantioselective Syntheses of (<i>Z</i>)-1,3-Butadienyl-2-carbinols via Brønsted Acid Catalysis — Ming Chen · Organic Letters (2025) | TGRS Research Map | TGRS