Enantio- and diastereoselective hydrogenation of a fluorinated diketone

Matthew L. Clarke; Marcia B. France; Fergus R. Knight; Jamie J. R. Frew; Geoffrey J. Roff

doi:10.1055/s-2007-982566

Enantio- and diastereoselective hydrogenation of a fluorinated diketone

Matthew L. Clarke, Marcia B. France, Fergus R. Knight, Jamie J. R. Frew, Geoffrey J. Roff

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

Abstract

Asymmetric hydrogenation of dibenzoyl-difluoromethane has been studied for the first time. In contrast to BINAL-H, baker's yeast and CBS reduction procedures, ruthenium-catalysed hydrogenation using axially chiral diphosphine ligands provides excellent yield, diastereoselectivity and good enantioselectivity (LIP to 72% ee). Enantiomer enrichment by recrystallisation allows for the pure fluorinated diol to be isolated as a single enantiomer in moderate yield.

Original language	English
Pages (from-to)	1739-1741
Number of pages	3
Journal	Synlett
DOIs	https://doi.org/10.1055/s-2007-982566
Publication status	Published - 3 Jul 2007

Keywords

homogeneous catalysis
hydrogenation
asymmetric synthesis
diols
organofluorine compounds
ASYMMETRIC HYDROGENATION
ABSOLUTE-CONFIGURATION
KETONES
HYDROFORMYLATION
REDUCTION
CATALYSIS
CHEMISTRY
ESTERS
LIGAND

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title = "Enantio- and diastereoselective hydrogenation of a fluorinated diketone",

abstract = "Asymmetric hydrogenation of dibenzoyl-difluoromethane has been studied for the first time. In contrast to BINAL-H, baker's yeast and CBS reduction procedures, ruthenium-catalysed hydrogenation using axially chiral diphosphine ligands provides excellent yield, diastereoselectivity and good enantioselectivity (LIP to 72% ee). Enantiomer enrichment by recrystallisation allows for the pure fluorinated diol to be isolated as a single enantiomer in moderate yield.",

keywords = "homogeneous catalysis, hydrogenation, asymmetric synthesis, diols, organofluorine compounds, ASYMMETRIC HYDROGENATION, ABSOLUTE-CONFIGURATION, KETONES, HYDROFORMYLATION, REDUCTION, CATALYSIS, CHEMISTRY, ESTERS, LIGAND",

author = "Clarke, {Matthew L.} and France, {Marcia B.} and Knight, {Fergus R.} and Frew, {Jamie J. R.} and Roff, {Geoffrey J.}",

year = "2007",

month = jul,

day = "3",

doi = "10.1055/s-2007-982566",

language = "English",

pages = "1739--1741",

journal = "Synlett",

issn = "0936-5214",

publisher = "Georg Thieme Verlag",

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T1 - Enantio- and diastereoselective hydrogenation of a fluorinated diketone

AU - Clarke, Matthew L.

AU - France, Marcia B.

AU - Knight, Fergus R.

AU - Frew, Jamie J. R.

AU - Roff, Geoffrey J.

PY - 2007/7/3

Y1 - 2007/7/3

N2 - Asymmetric hydrogenation of dibenzoyl-difluoromethane has been studied for the first time. In contrast to BINAL-H, baker's yeast and CBS reduction procedures, ruthenium-catalysed hydrogenation using axially chiral diphosphine ligands provides excellent yield, diastereoselectivity and good enantioselectivity (LIP to 72% ee). Enantiomer enrichment by recrystallisation allows for the pure fluorinated diol to be isolated as a single enantiomer in moderate yield.

AB - Asymmetric hydrogenation of dibenzoyl-difluoromethane has been studied for the first time. In contrast to BINAL-H, baker's yeast and CBS reduction procedures, ruthenium-catalysed hydrogenation using axially chiral diphosphine ligands provides excellent yield, diastereoselectivity and good enantioselectivity (LIP to 72% ee). Enantiomer enrichment by recrystallisation allows for the pure fluorinated diol to be isolated as a single enantiomer in moderate yield.

KW - homogeneous catalysis

KW - hydrogenation

KW - asymmetric synthesis

KW - diols

KW - organofluorine compounds

KW - ASYMMETRIC HYDROGENATION

KW - ABSOLUTE-CONFIGURATION

KW - KETONES

KW - HYDROFORMYLATION

KW - REDUCTION

KW - CATALYSIS

KW - CHEMISTRY

KW - ESTERS

KW - LIGAND

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U2 - 10.1055/s-2007-982566

DO - 10.1055/s-2007-982566

M3 - Article

SN - 0936-5214

SP - 1739

EP - 1741

JO - Synlett

JF - Synlett

ER -

Enantio- and diastereoselective hydrogenation of a fluorinated diketone

Abstract

Keywords

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