Pd-Catalyzed Synthesis of γ-Keto Esters as Key Intermediates for the Synthesis of γ-Hydroxybutenolides

Mathias Schacht; Djawid Mohammadi; Nina Schützenmeister

doi:10.1002/ejoc.201900023

Pd-Catalyzed Synthesis of γ-Keto Esters as Key Intermediates for the Synthesis of γ-Hydroxybutenolides

Mathias Schacht, Djawid Mohammadi, Nina Schützenmeister (Corresponding author)

Publications: Contribution to journal › Article › Peer Reviewed

Abstract

We herein report a robust and safe palladium catalyzed domino-carbonylation/Suzuki–Miyaura cross-coupling reaction of vinyltosylates with arylboronic acids using Mo(CO) ₆ as CO-source. The derived γ-keto ester were subsequently cyclized under acidic conditions to obtain γ-hydroxybutenolides, an important structural motif, which occurs in biologically active natural products.

Original language	English
Pages (from-to)	2587-2591
Number of pages	5
Journal	European Journal of Organic Chemistry
Volume	2019
Issue number	15
DOIs	https://doi.org/10.1002/ejoc.201900023
Publication status	Published - 24 Apr 2019
Externally published	Yes

Austrian Fields of Science 2012

104013 Natural product chemistry
104008 Catalysis
104015 Organic chemistry
301207 Pharmaceutical chemistry

Keywords

Boronic acids
Carbonylation
Catalysis
Cross-coupling
Vinyltosylates

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10.1002/ejoc.201900023

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title = "Pd-Catalyzed Synthesis of γ-Keto Esters as Key Intermediates for the Synthesis of γ-Hydroxybutenolides",

abstract = "We herein report a robust and safe palladium catalyzed domino-carbonylation/Suzuki–Miyaura cross-coupling reaction of vinyltosylates with arylboronic acids using Mo(CO) 6 as CO-source. The derived γ-keto ester were subsequently cyclized under acidic conditions to obtain γ-hydroxybutenolides, an important structural motif, which occurs in biologically active natural products. ",

keywords = "Boronic acids, Carbonylation, Catalysis, Cross-coupling, Vinyltosylates",

author = "Mathias Schacht and Djawid Mohammadi and Nina Sch{\"u}tzenmeister",

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year = "2019",

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doi = "10.1002/ejoc.201900023",

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T1 - Pd-Catalyzed Synthesis of γ-Keto Esters as Key Intermediates for the Synthesis of γ-Hydroxybutenolides

AU - Schacht, Mathias

AU - Mohammadi, Djawid

AU - Schützenmeister, Nina

PY - 2019/4/24

Y1 - 2019/4/24

N2 - We herein report a robust and safe palladium catalyzed domino-carbonylation/Suzuki–Miyaura cross-coupling reaction of vinyltosylates with arylboronic acids using Mo(CO) 6 as CO-source. The derived γ-keto ester were subsequently cyclized under acidic conditions to obtain γ-hydroxybutenolides, an important structural motif, which occurs in biologically active natural products.

AB - We herein report a robust and safe palladium catalyzed domino-carbonylation/Suzuki–Miyaura cross-coupling reaction of vinyltosylates with arylboronic acids using Mo(CO) 6 as CO-source. The derived γ-keto ester were subsequently cyclized under acidic conditions to obtain γ-hydroxybutenolides, an important structural motif, which occurs in biologically active natural products.

KW - Boronic acids

KW - Carbonylation

KW - Catalysis

KW - Cross-coupling

KW - Vinyltosylates

UR - https://www.scopus.com/pages/publications/85061509447

U2 - 10.1002/ejoc.201900023

DO - 10.1002/ejoc.201900023

M3 - Article

SN - 1434-193X

VL - 2019

SP - 2587

EP - 2591

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

IS - 15

ER -

Pd-Catalyzed Synthesis of γ-Keto Esters as Key Intermediates for the Synthesis of γ-Hydroxybutenolides

Abstract

Austrian Fields of Science 2012

Keywords

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