DNA-based asymmetric organometallic catalysis in water

Jens Oelerich; Gerard Roelfes

doi:10.1039/c3sc00100h

DNA-based asymmetric organometallic catalysis in water

Jens Oelerich, Gerard Roelfes^*

^*Corresponding author for this work

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

57 Citations (Scopus)

521 Downloads (Pure)

Abstract

Here, the first examples of DNA-based organometallic catalysis in water that give rise to high enantioselectivities are described. Copper complexes of strongly intercalating ligands were found to enable the asymmetric intramolecular cyclopropanation of alpha-diazo-beta-keto sulfones in water. Up to 84% ee was achieved, in the presence of salmon testes DNA as the only source of chirality, using dipyrido [3,2-a: 2',3'-c] phenazine (dppz) derivatives as ligands.

Original language	English
Pages (from-to)	2013-2017
Number of pages	5
Journal	Chemical Science
Volume	4
Issue number	5
DOIs	https://doi.org/10.1039/c3sc00100h
Publication status	Published - 15-Mar-2013

Keywords

TRANSITION-METAL CATALYSIS
MONODENTATE P-LIGANDS
IN-SITU GENERATION
CYCLOPROPANATION REACTIONS
INTRAMOLECULAR CYCLOPROPANATION
COMPLEXES
ENANTIOSELECTIVITY
MEDIA
HYDROCHLORIDE
INTERCALATORS

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Cite this

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title = "DNA-based asymmetric organometallic catalysis in water",

abstract = "Here, the first examples of DNA-based organometallic catalysis in water that give rise to high enantioselectivities are described. Copper complexes of strongly intercalating ligands were found to enable the asymmetric intramolecular cyclopropanation of alpha-diazo-beta-keto sulfones in water. Up to 84% ee was achieved, in the presence of salmon testes DNA as the only source of chirality, using dipyrido [3,2-a: 2',3'-c] phenazine (dppz) derivatives as ligands.",

keywords = "TRANSITION-METAL CATALYSIS, MONODENTATE P-LIGANDS, IN-SITU GENERATION, CYCLOPROPANATION REACTIONS, INTRAMOLECULAR CYCLOPROPANATION, COMPLEXES, ENANTIOSELECTIVITY, MEDIA, HYDROCHLORIDE, INTERCALATORS",

author = "Jens Oelerich and Gerard Roelfes",

year = "2013",

month = mar,

day = "15",

doi = "10.1039/c3sc00100h",

language = "English",

volume = "4",

pages = "2013--2017",

journal = "Chemical Science",

issn = "2041-6520",

publisher = "ROYAL SOC CHEMISTRY",

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TY - JOUR

T1 - DNA-based asymmetric organometallic catalysis in water

AU - Oelerich, Jens

AU - Roelfes, Gerard

PY - 2013/3/15

Y1 - 2013/3/15

N2 - Here, the first examples of DNA-based organometallic catalysis in water that give rise to high enantioselectivities are described. Copper complexes of strongly intercalating ligands were found to enable the asymmetric intramolecular cyclopropanation of alpha-diazo-beta-keto sulfones in water. Up to 84% ee was achieved, in the presence of salmon testes DNA as the only source of chirality, using dipyrido [3,2-a: 2',3'-c] phenazine (dppz) derivatives as ligands.

AB - Here, the first examples of DNA-based organometallic catalysis in water that give rise to high enantioselectivities are described. Copper complexes of strongly intercalating ligands were found to enable the asymmetric intramolecular cyclopropanation of alpha-diazo-beta-keto sulfones in water. Up to 84% ee was achieved, in the presence of salmon testes DNA as the only source of chirality, using dipyrido [3,2-a: 2',3'-c] phenazine (dppz) derivatives as ligands.

KW - TRANSITION-METAL CATALYSIS

KW - MONODENTATE P-LIGANDS

KW - IN-SITU GENERATION

KW - CYCLOPROPANATION REACTIONS

KW - INTRAMOLECULAR CYCLOPROPANATION

KW - COMPLEXES

KW - ENANTIOSELECTIVITY

KW - MEDIA

KW - HYDROCHLORIDE

KW - INTERCALATORS

U2 - 10.1039/c3sc00100h

DO - 10.1039/c3sc00100h

M3 - Article

VL - 4

SP - 2013

EP - 2017

JO - Chemical Science

JF - Chemical Science

SN - 2041-6520

IS - 5

ER -