Palladium-catalyzed stereoselective domino arylation-acylation: an entry to chiral tetrahydrofluorenone scaffolds

Petter Dunås; Andrew J. Paterson; Gabriele Kociok-Köhn; Martin Rahm; Simon E. Lewis; Nina Kann

doi:10.1039/d1cc02160e

Palladium-catalyzed stereoselective domino arylation-acylation: an entry to chiral tetrahydrofluorenone scaffolds

Petter Dunås, Andrew J. Paterson, Gabriele Kociok-Köhn, Martin Rahm, Simon E. Lewis, Nina Kann

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

2 Citations (SciVal)

43 Downloads (Pure)

Abstract

A palladium-catalyzed domino arylation-cyclization of biocatalytically derived cyclic 1,3-dienes is demonstrated. The reaction introduces a high degree of structural complexity in a single step, giving access to tricyclic tetrahydrofluorenones with full regio- and stereoselectivity. The transformation proceeds through a novel acylation-terminated Heck-type sequence, and quantum chemical calculations indicate that C-H activation is involved in the terminating acylation step.

Original language	English
Pages (from-to)	6518-6521
Number of pages	4
Journal	Chemical Communications
Volume	57
Issue number	53
Early online date	2 Jun 2021
DOIs	https://doi.org/10.1039/d1cc02160e
Publication status	Published - 7 Jul 2021

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

Access to Document

10.1039/d1cc02160eLicence: CC BY

___ChemCommun__2021__57__6518___Licence: CC BY

Cite this

@article{61c264a1dd6f4d14a85d2118f184b2bc,

title = "Palladium-catalyzed stereoselective domino arylation-acylation: an entry to chiral tetrahydrofluorenone scaffolds",

abstract = "A palladium-catalyzed domino arylation-cyclization of biocatalytically derived cyclic 1,3-dienes is demonstrated. The reaction introduces a high degree of structural complexity in a single step, giving access to tricyclic tetrahydrofluorenones with full regio- and stereoselectivity. The transformation proceeds through a novel acylation-terminated Heck-type sequence, and quantum chemical calculations indicate that C-H activation is involved in the terminating acylation step.",

author = "Petter Dun{\aa}s and Paterson, {Andrew J.} and Gabriele Kociok-K{\"o}hn and Martin Rahm and Lewis, {Simon E.} and Nina Kann",

year = "2021",

month = jul,

day = "7",

doi = "10.1039/d1cc02160e",

language = "English",

volume = "57",

pages = "6518--6521",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "53",

}

TY - JOUR

T1 - Palladium-catalyzed stereoselective domino arylation-acylation

T2 - an entry to chiral tetrahydrofluorenone scaffolds

AU - Dunås, Petter

AU - Paterson, Andrew J.

AU - Kociok-Köhn, Gabriele

AU - Rahm, Martin

AU - Lewis, Simon E.

AU - Kann, Nina

PY - 2021/7/7

Y1 - 2021/7/7

N2 - A palladium-catalyzed domino arylation-cyclization of biocatalytically derived cyclic 1,3-dienes is demonstrated. The reaction introduces a high degree of structural complexity in a single step, giving access to tricyclic tetrahydrofluorenones with full regio- and stereoselectivity. The transformation proceeds through a novel acylation-terminated Heck-type sequence, and quantum chemical calculations indicate that C-H activation is involved in the terminating acylation step.

AB - A palladium-catalyzed domino arylation-cyclization of biocatalytically derived cyclic 1,3-dienes is demonstrated. The reaction introduces a high degree of structural complexity in a single step, giving access to tricyclic tetrahydrofluorenones with full regio- and stereoselectivity. The transformation proceeds through a novel acylation-terminated Heck-type sequence, and quantum chemical calculations indicate that C-H activation is involved in the terminating acylation step.

UR - http://www.scopus.com/inward/record.url?scp=85109036338&partnerID=8YFLogxK

U2 - 10.1039/d1cc02160e

DO - 10.1039/d1cc02160e

M3 - Article

C2 - 34105551

AN - SCOPUS:85109036338

SN - 1359-7345

VL - 57

SP - 6518

EP - 6521

JO - Chemical Communications

JF - Chemical Communications

IS - 53

ER -

Palladium-catalyzed stereoselective domino arylation-acylation: an entry to chiral tetrahydrofluorenone scaffolds

Abstract

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this