ENANTIOSELECTIVE [2+2+2] CYCLOISOMERISATION OF ALKYNES IN THE SYNTHESIS OF HELICENES: THE SEARCH FOR EFFECTIVE CHIRAL LIGANDS

Irena G. Stara; Angelina Andronova; Adrian Kollarovic; Stepan Vyskocil; Sylvain Juge; Guy C. Lloyd-Jones; Patrick J. Guiry; Ivo Stary

doi:10.1135/cccc2011177

ENANTIOSELECTIVE [2+2+2] CYCLOISOMERISATION OF ALKYNES IN THE SYNTHESIS OF HELICENES: THE SEARCH FOR EFFECTIVE CHIRAL LIGANDS

Irena G. Stara^*, Angelina Andronova, Adrian Kollarovic, Stepan Vyskocil, Sylvain Juge, Guy C. Lloyd-Jones, Patrick J. Guiry, Ivo Stary

^*Corresponding author for this work

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

Abstract / Description of output

The enantioselective [2+2+2] cycloisomerisation of the aromatic triynes under nickel(0) catalysis to afford nonracemic [6]- and [7]helicene derivatives has been systematically studied. A collection of mono-and bidentate phosphines, phosphites, phosphinites and phosphinous amides possessing stereogenic units such as chiral centre, axis or plane (or their combinations) has been tested and axially chiral binaphthyl-derived monodentate MOP-type phosphine ligands were the optimal class of ligands. Nickel complexes of these ligands afforded nonracemic tetrahydro [6]helicene in up to 64% ee in a model reaction.

Original language	English
Pages (from-to)	2005-2022
Number of pages	18
Journal	Collection of czechoslovak chemical communications
Volume	76
Issue number	12
DOIs	https://doi.org/10.1135/cccc2011177
Publication status	Published - 2011

Keywords / Materials (for Non-textual outputs)

Helicenes
Alkynes
Cycloisomerisation
Nickel catalysis
Phosphorus ligands
Enantioselectivity
Chirality
Asymmetric catalysis
ASYMMETRIC CATALYSIS
QUINAZOLINAP LIGANDS
PHOSPHINITE LIGANDS
COUPLING REACTIONS
AROMATIC TRIYNES
RESOLUTION
MOLECULES
ROUTE
HYDROGENATION
HYDROBORATION

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@article{0d623d0b04f0454986fc2c78698bbb8e,

title = "ENANTIOSELECTIVE [2+2+2] CYCLOISOMERISATION OF ALKYNES IN THE SYNTHESIS OF HELICENES: THE SEARCH FOR EFFECTIVE CHIRAL LIGANDS",

abstract = "The enantioselective [2+2+2] cycloisomerisation of the aromatic triynes under nickel(0) catalysis to afford nonracemic [6]- and [7]helicene derivatives has been systematically studied. A collection of mono-and bidentate phosphines, phosphites, phosphinites and phosphinous amides possessing stereogenic units such as chiral centre, axis or plane (or their combinations) has been tested and axially chiral binaphthyl-derived monodentate MOP-type phosphine ligands were the optimal class of ligands. Nickel complexes of these ligands afforded nonracemic tetrahydro [6]helicene in up to 64% ee in a model reaction.",

keywords = "Helicenes, Alkynes, Cycloisomerisation, Nickel catalysis, Phosphorus ligands, Enantioselectivity, Chirality, Asymmetric catalysis, ASYMMETRIC CATALYSIS, QUINAZOLINAP LIGANDS, PHOSPHINITE LIGANDS, COUPLING REACTIONS, AROMATIC TRIYNES, RESOLUTION, MOLECULES, ROUTE, HYDROGENATION, HYDROBORATION",

author = "Stara, {Irena G.} and Angelina Andronova and Adrian Kollarovic and Stepan Vyskocil and Sylvain Juge and Lloyd-Jones, {Guy C.} and Guiry, {Patrick J.} and Ivo Stary",

year = "2011",

doi = "10.1135/cccc2011177",

language = "English",

volume = "76",

pages = "2005--2022",

journal = "Collection of czechoslovak chemical communications",

issn = "0010-0765",

publisher = "Czech Academy of Sciences",

number = "12",

}

TY - JOUR

T1 - ENANTIOSELECTIVE [2+2+2] CYCLOISOMERISATION OF ALKYNES IN THE SYNTHESIS OF HELICENES

T2 - THE SEARCH FOR EFFECTIVE CHIRAL LIGANDS

AU - Stara, Irena G.

AU - Andronova, Angelina

AU - Kollarovic, Adrian

AU - Vyskocil, Stepan

AU - Juge, Sylvain

AU - Lloyd-Jones, Guy C.

AU - Guiry, Patrick J.

AU - Stary, Ivo

PY - 2011

Y1 - 2011

N2 - The enantioselective [2+2+2] cycloisomerisation of the aromatic triynes under nickel(0) catalysis to afford nonracemic [6]- and [7]helicene derivatives has been systematically studied. A collection of mono-and bidentate phosphines, phosphites, phosphinites and phosphinous amides possessing stereogenic units such as chiral centre, axis or plane (or their combinations) has been tested and axially chiral binaphthyl-derived monodentate MOP-type phosphine ligands were the optimal class of ligands. Nickel complexes of these ligands afforded nonracemic tetrahydro [6]helicene in up to 64% ee in a model reaction.

AB - The enantioselective [2+2+2] cycloisomerisation of the aromatic triynes under nickel(0) catalysis to afford nonracemic [6]- and [7]helicene derivatives has been systematically studied. A collection of mono-and bidentate phosphines, phosphites, phosphinites and phosphinous amides possessing stereogenic units such as chiral centre, axis or plane (or their combinations) has been tested and axially chiral binaphthyl-derived monodentate MOP-type phosphine ligands were the optimal class of ligands. Nickel complexes of these ligands afforded nonracemic tetrahydro [6]helicene in up to 64% ee in a model reaction.

KW - Helicenes

KW - Alkynes

KW - Cycloisomerisation

KW - Nickel catalysis

KW - Phosphorus ligands

KW - Enantioselectivity

KW - Chirality

KW - Asymmetric catalysis

KW - ASYMMETRIC CATALYSIS

KW - QUINAZOLINAP LIGANDS

KW - PHOSPHINITE LIGANDS

KW - COUPLING REACTIONS

KW - AROMATIC TRIYNES

KW - RESOLUTION

KW - MOLECULES

KW - ROUTE

KW - HYDROGENATION

KW - HYDROBORATION

U2 - 10.1135/cccc2011177

DO - 10.1135/cccc2011177

M3 - Article

SN - 0010-0765

VL - 76

SP - 2005

EP - 2022

JO - Collection of czechoslovak chemical communications

JF - Collection of czechoslovak chemical communications

IS - 12

ER -

ENANTIOSELECTIVE [2+2+2] CYCLOISOMERISATION OF ALKYNES IN THE SYNTHESIS OF HELICENES: THE SEARCH FOR EFFECTIVE CHIRAL LIGANDS

Abstract / Description of output

Keywords / Materials (for Non-textual outputs)

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