Asymmetric Isochalcogenourea-Catalyzed Synthesis of 3,4-Dihydropyrans via (4+2)-Cycloadditions of Ethyl But-3-ynoate with Michael Acceptors

Mario Hofer; Magdalena Piringer; Anna Scheucher; Lukas S. Vogl; Mario Waser

doi:10.1055/a-2659-8340

Asymmetric Isochalcogenourea-Catalyzed Synthesis of 3,4-Dihydropyrans via (4+2)-Cycloadditions of Ethyl But-3-ynoate with Michael Acceptors

Mario Hofer
, Magdalena Piringer
, Anna Scheucher
, Lukas S. Vogl
, Mario Waser^*

^*Corresponding author for this work

Institute of Organic Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

We herein report the use of ethyl but-3-ynoate as a C2 building block for asymmetric (4+2)-heterocycloadditions with various Michael acceptors. Upon using chiral isochalcogenoureas as Lewis base catalysts, these reactions can be carried out with good to excellent control of the regioselectivity, diastereoselectivity, and enantioselectivity.

Original language	English
Pages (from-to)	3241-3244
Number of pages	4
Journal	Synlett
Volume	36
Issue number	19
Early online date	18 Aug 2025
DOIs	https://doi.org/10.1055/a-2659-8340
Publication status	Published - 01 Dec 2025

Fields of science

104015 Organic chemistry
104026 Spectroscopy
104 Chemistry
104021 Structural chemistry

JKU Focus areas

Sustainable Development: Responsible Technologies and Management

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10.1055/a-2659-8340

http://www.thieme-connect.de/DOI/DOI?10.1055/a-2659-8340

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title = "Asymmetric Isochalcogenourea-Catalyzed Synthesis of 3,4-Dihydropyrans via (4+2)-Cycloadditions of Ethyl But-3-ynoate with Michael Acceptors",

abstract = "We herein report the use of ethyl but-3-ynoate as a C2 building block for asymmetric (4+2)-heterocycloadditions with various Michael acceptors. Upon using chiral isochalcogenoureas as Lewis base catalysts, these reactions can be carried out with good to excellent control of the regioselectivity, diastereoselectivity, and enantioselectivity.",

author = "Mario Hofer and Magdalena Piringer and Anna Scheucher and Vogl, \{Lukas S.\} and Mario Waser",

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language = "English",

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T1 - Asymmetric Isochalcogenourea-Catalyzed Synthesis of 3,4-Dihydropyrans via (4+2)-Cycloadditions of Ethyl But-3-ynoate with Michael Acceptors

AU - Hofer, Mario

AU - Piringer, Magdalena

AU - Scheucher, Anna

AU - Vogl, Lukas S.

AU - Waser, Mario

PY - 2025/12/1

Y1 - 2025/12/1

N2 - We herein report the use of ethyl but-3-ynoate as a C2 building block for asymmetric (4+2)-heterocycloadditions with various Michael acceptors. Upon using chiral isochalcogenoureas as Lewis base catalysts, these reactions can be carried out with good to excellent control of the regioselectivity, diastereoselectivity, and enantioselectivity.

AB - We herein report the use of ethyl but-3-ynoate as a C2 building block for asymmetric (4+2)-heterocycloadditions with various Michael acceptors. Upon using chiral isochalcogenoureas as Lewis base catalysts, these reactions can be carried out with good to excellent control of the regioselectivity, diastereoselectivity, and enantioselectivity.

UR - https://www.scopus.com/pages/publications/105021920013

U2 - 10.1055/a-2659-8340

DO - 10.1055/a-2659-8340

M3 - Article

C2 - 40837029

SN - 0936-5214

VL - 36

SP - 3241

EP - 3244

JO - Synlett

JF - Synlett

IS - 19

ER -

Asymmetric Isochalcogenourea-Catalyzed Synthesis of 3,4-Dihydropyrans via (4+2)-Cycloadditions of Ethyl But-3-ynoate with Michael Acceptors

Abstract

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