Asymmetric (4 + 2) Cyclization of γ-Substituted Propargyl Carboxylates with <i>o</i>-Quinone Methides Catalyzed by Chiral Tertiary Phosphine

An enantioselective (4 + 2) cycloaddition reaction of γ-aryl-substituted alkynyl carboxylates with <i>ortho</i>-quinone methides (<i>o</i>-QMs) was developed for the first time in the catalysis of (<i>R</i>,<i>R</i>)-DIPAMP. A series of chiral 4H-chromenes derivatives were available in good yields (62%-89% yield) and excellent enantioselectivities (up to 96% enantiomeric excess). Those obtained products could be further transformed to other derivatives.

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Publication Details

Journal
Organic Letters
Published
2025-08-04
DOI
https://doi.org/10.1021/acs.orglett.5c02279
Citations
2
Primary Topic
Synthesis of Indole Derivatives
Type
article
Field-Weighted Citation Impact
1.87

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article

Asymmetric (4 + 2) Cyclization of γ-Substituted Propargyl Carboxylates with o-Quinone Methides Catalyzed by Chiral Tertiary Phosphine

Yungui Peng, Rui She, Guihua Chen, Chaowei Bi et al.
2 citations
Organic Letters
Synthesis of Indole Derivatives
1.87
article

Asymmetric (4 + 2) Cyclization of γ-Substituted Propargyl Carboxylates with o-Quinone Methides Catalyzed by Chiral Tertiary Phosphine

Yungui Peng, Rui She, Guihua Chen, Chaowei Bi, Yuxing Fan, Hongyu Liu
article en
2 citations

Abstract

An enantioselective (4 + 2) cycloaddition reaction of γ-aryl-substituted alkynyl carboxylates with <i>ortho</i>-quinone methides (<i>o</i>-QMs) was developed for the first time in the catalysis of (<i>R</i>,<i>R</i>)-DIPAMP. A series of chiral 4H-chromenes derivatives were available in good yields (62%-89% yield) and excellent enantioselectivities (up to 96% enantiomeric excess). Those obtained products could be further transformed to other derivatives.

Organic LettersVol. 27(32)
Southwest University (CN), Chongqing Municipal Government (CN)
Fundamental Research Funds for the Central Universities
Clean water and sanitation
Openalex Percentile: Top 14%
Synthesis of Indole Derivatives
1.87
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Asymmetric (4 + 2) Cyclization of γ-Substituted Propargyl Carboxylates with <i>o</i>-Quinone Methides Catalyzed by Chiral Tertiary Phosphine — Yungui Peng, Rui She, et al. · Organic Letters (2025) | TGRS Research Map | TGRS