Enantioselective Au(i)-catalyzed tandem reactions between 2-alkynyl enones and naphthols by the tethered counterion-directed catalysis strategy

Yunliang Yu; Nazarii Sabat; Meriem Daghmoum; Zhenhao Zhang; Pascal Retailleau; Gilles Frison; Angela Marinetti; Xavier Guinchard

doi:10.1039/d3qo00415e

Enantioselective Au(i)-catalyzed tandem reactions between 2-alkynyl enones and naphthols by the tethered counterion-directed catalysis strategy

Yunliang Yu
, Nazarii Sabat
, Meriem Daghmoum
, Zhenhao Zhang
, Pascal Retailleau
, Gilles Frison
, Angela Marinetti
, Xavier Guinchard

École Polytechnique

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

Abstract

Enantioselective tandem cycloisomerization/addition reactions of 2-alkynyl enones with 1- and 2-naphthols have been investigated using gold(i) catalysts featuring hybrid phosphine-phosphoric acid chiral ligands, according to the tethered counterion-directed catalysis (TCDC) strategy. The reactions occur at low catalyst loading (0.2-1 mol%) without silver additives, and the naphthols act as both O- and C-nucleophiles, leading to the corresponding addition products with high enantioselectivity. DFT calculations enlighten these processes.

Original language	English
Pages (from-to)	2936-2942
Number of pages	7
Journal	Organic Chemistry Frontiers
Volume	10
Issue number	12
DOIs	https://doi.org/10.1039/d3qo00415e
Publication status	Published - 28 Apr 2023

Access to Document

10.1039/d3qo00415e

Cite this

@article{4015d6e690164ca9a18477698805def0,

title = "Enantioselective Au(i)-catalyzed tandem reactions between 2-alkynyl enones and naphthols by the tethered counterion-directed catalysis strategy",

abstract = "Enantioselective tandem cycloisomerization/addition reactions of 2-alkynyl enones with 1- and 2-naphthols have been investigated using gold(i) catalysts featuring hybrid phosphine-phosphoric acid chiral ligands, according to the tethered counterion-directed catalysis (TCDC) strategy. The reactions occur at low catalyst loading (0.2-1 mol\%) without silver additives, and the naphthols act as both O- and C-nucleophiles, leading to the corresponding addition products with high enantioselectivity. DFT calculations enlighten these processes.",

author = "Yunliang Yu and Nazarii Sabat and Meriem Daghmoum and Zhenhao Zhang and Pascal Retailleau and Gilles Frison and Angela Marinetti and Xavier Guinchard",

note = "Publisher Copyright: {\textcopyright} 2023 The Royal Society of Chemistry.",

year = "2023",

month = apr,

day = "28",

doi = "10.1039/d3qo00415e",

language = "English",

volume = "10",

pages = "2936--2942",

journal = "Organic Chemistry Frontiers",

issn = "2052-4110",

number = "12",

}

TY - JOUR

T1 - Enantioselective Au(i)-catalyzed tandem reactions between 2-alkynyl enones and naphthols by the tethered counterion-directed catalysis strategy

AU - Yu, Yunliang

AU - Sabat, Nazarii

AU - Daghmoum, Meriem

AU - Zhang, Zhenhao

AU - Retailleau, Pascal

AU - Frison, Gilles

AU - Marinetti, Angela

AU - Guinchard, Xavier

PY - 2023/4/28

Y1 - 2023/4/28

N2 - Enantioselective tandem cycloisomerization/addition reactions of 2-alkynyl enones with 1- and 2-naphthols have been investigated using gold(i) catalysts featuring hybrid phosphine-phosphoric acid chiral ligands, according to the tethered counterion-directed catalysis (TCDC) strategy. The reactions occur at low catalyst loading (0.2-1 mol%) without silver additives, and the naphthols act as both O- and C-nucleophiles, leading to the corresponding addition products with high enantioselectivity. DFT calculations enlighten these processes.

AB - Enantioselective tandem cycloisomerization/addition reactions of 2-alkynyl enones with 1- and 2-naphthols have been investigated using gold(i) catalysts featuring hybrid phosphine-phosphoric acid chiral ligands, according to the tethered counterion-directed catalysis (TCDC) strategy. The reactions occur at low catalyst loading (0.2-1 mol%) without silver additives, and the naphthols act as both O- and C-nucleophiles, leading to the corresponding addition products with high enantioselectivity. DFT calculations enlighten these processes.

UR - https://www.scopus.com/pages/publications/85159644447

U2 - 10.1039/d3qo00415e

DO - 10.1039/d3qo00415e

M3 - Article

AN - SCOPUS:85159644447

SN - 2052-4110

VL - 10

SP - 2936

EP - 2942

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 12

ER -

Enantioselective Au(i)-catalyzed tandem reactions between 2-alkynyl enones and naphthols by the tethered counterion-directed catalysis strategy

Abstract

Access to Document

Other files and links

Fingerprint

Cite this