Chiral calix[4]arene-based diphosphites as ligands in the asymmetric hydrogenation of prochiral olefins

Angelica Marson; Zoraida Freixa; Paul C. J. Kamer; Piet W. N. M. van Leeuwen

doi:10.1002/ejic.200700764

Chiral calix[4]arene-based diphosphites as ligands in the asymmetric hydrogenation of prochiral olefins

Angelica Marson, Zoraida Freixa, Paul C. J. Kamer, Piet W. N. M. van Leeuwen

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

Abstract

Chiral calixarene-based diphosphite ligands 3a-d have been obtained via lower-rim functionalisation of the p-tert-butylcalix[4]arene core. High enantiomeric excesses (up to 94 %) and good activities were obtained in the rhodium-catalyzed asymmetric hydrogenation of prochiral olefins with TADDOL-containing diphosphites 3c,d. This is the first example of chiral calix[4]arene-modified ligands that induce high enantioselectivity in metal-catalysed asymmetric reactions.

Original language	English
Pages (from-to)	4587-4591
Number of pages	5
Journal	European Journal of Inorganic Chemistry
DOIs	https://doi.org/10.1002/ejic.200700764
Publication status	Published - Oct 2007

Keywords

homogeneous catalysis
stereoselective catalysis
asymmetric hydrogenation
calixarenes
diphosphites
RHODIUM-CATALYZED HYDROFORMYLATION
ENANTIOSELECTIVE CATALYSIS
PHOSPHORUS LIGANDS
NBD PRECATALYSTS
COMPLEXES
PHOSPHITES
1-OCTENE
TADDOL
COD
REGIOSELECTIVITY

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@article{921038c4468847b6aff75333da4895dc,

title = "Chiral calix[4]arene-based diphosphites as ligands in the asymmetric hydrogenation of prochiral olefins",

abstract = "Chiral calixarene-based diphosphite ligands 3a-d have been obtained via lower-rim functionalisation of the p-tert-butylcalix[4]arene core. High enantiomeric excesses (up to 94 %) and good activities were obtained in the rhodium-catalyzed asymmetric hydrogenation of prochiral olefins with TADDOL-containing diphosphites 3c,d. This is the first example of chiral calix[4]arene-modified ligands that induce high enantioselectivity in metal-catalysed asymmetric reactions.",

keywords = "homogeneous catalysis, stereoselective catalysis, asymmetric hydrogenation, calixarenes, diphosphites, RHODIUM-CATALYZED HYDROFORMYLATION, ENANTIOSELECTIVE CATALYSIS, PHOSPHORUS LIGANDS, NBD PRECATALYSTS, COMPLEXES, PHOSPHITES, 1-OCTENE, TADDOL, COD, REGIOSELECTIVITY",

author = "Angelica Marson and Zoraida Freixa and Kamer, {Paul C. J.} and {van Leeuwen}, {Piet W. N. M.}",

year = "2007",

month = oct,

doi = "10.1002/ejic.200700764",

language = "English",

pages = "4587--4591",

journal = "European Journal of Inorganic Chemistry",

issn = "1434-1948",

publisher = "Wiley-Blackwell",

}

TY - JOUR

T1 - Chiral calix[4]arene-based diphosphites as ligands in the asymmetric hydrogenation of prochiral olefins

AU - Marson, Angelica

AU - Freixa, Zoraida

AU - Kamer, Paul C. J.

AU - van Leeuwen, Piet W. N. M.

PY - 2007/10

Y1 - 2007/10

N2 - Chiral calixarene-based diphosphite ligands 3a-d have been obtained via lower-rim functionalisation of the p-tert-butylcalix[4]arene core. High enantiomeric excesses (up to 94 %) and good activities were obtained in the rhodium-catalyzed asymmetric hydrogenation of prochiral olefins with TADDOL-containing diphosphites 3c,d. This is the first example of chiral calix[4]arene-modified ligands that induce high enantioselectivity in metal-catalysed asymmetric reactions.

AB - Chiral calixarene-based diphosphite ligands 3a-d have been obtained via lower-rim functionalisation of the p-tert-butylcalix[4]arene core. High enantiomeric excesses (up to 94 %) and good activities were obtained in the rhodium-catalyzed asymmetric hydrogenation of prochiral olefins with TADDOL-containing diphosphites 3c,d. This is the first example of chiral calix[4]arene-modified ligands that induce high enantioselectivity in metal-catalysed asymmetric reactions.

KW - homogeneous catalysis

KW - stereoselective catalysis

KW - asymmetric hydrogenation

KW - calixarenes

KW - diphosphites

KW - RHODIUM-CATALYZED HYDROFORMYLATION

KW - ENANTIOSELECTIVE CATALYSIS

KW - PHOSPHORUS LIGANDS

KW - NBD PRECATALYSTS

KW - COMPLEXES

KW - PHOSPHITES

KW - 1-OCTENE

KW - TADDOL

KW - COD

KW - REGIOSELECTIVITY

UR - http://www.scopus.com/inward/record.url?scp=35348962558&partnerID=8YFLogxK

U2 - 10.1002/ejic.200700764

DO - 10.1002/ejic.200700764

M3 - Article

SN - 1434-1948

SP - 4587

EP - 4591

JO - European Journal of Inorganic Chemistry

JF - European Journal of Inorganic Chemistry

ER -

Chiral calix[4]arene-based diphosphites as ligands in the asymmetric hydrogenation of prochiral olefins

Abstract

Keywords

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