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Synlett

Volumn , Issue 11, 2007, Pages 1739-1741

Enantio- and diastereoselective hydrogenation of a fluorinated diketone

(5) Clarke, Matthew L b France, Marcia B a Knight, Fergus R b Frew, Jamie J R b Roff, Geoffrey J b

a WASHINGTON AND LEE UNIVERSITY (United States)

b UNIVERSITY OF ST ANDREWS (United Kingdom)

Author keywords

Asymmetric synthesis; Diols; Homogeneous catalysis; Hydrogenation; Organofluorine compounds

Indexed keywords

DIBENZOYL DIFLUOROMETHANE; DIKETONE; DIPHOSPHINE; LIGAND; PHOSPHINE DERIVATIVE; RUTHENIUM; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; CRYSTALLIZATION; ENANTIOSELECTIVITY; FLUORINATION; HYDROGENATION; REDUCTION; SACCHAROMYCES CEREVISIAE; STEREOCHEMISTRY;

EID: 34447502431 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-982566 Document Type: Article

Times cited : (10)

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- General Procedures for Catalyst Preparation Method 1: To a dried microwave tube was added benzeneruthenium chloride dimer (1.7 mg, 0.0034 mmol) and diphosphine (0.0068 mmol) and the air was evacuated and replaced with argon. To the mixture was added anhyd DMF (1 mL) and the mixture stirred under argon at 100°C for 10 min. The DMF was removed in vacuo at 50°C to give the catalyst. Method 2:14 To a dried microwave tube was added [RuCOD(η3-2-methyl-allyl)2, 4.6 mg, 0.014 mmol) and diphosphine (0.014 mmol) and the air displaced with argon. To this was added anhyd acetone (1 mL) followed by HBr solution [122 μL, 0.035 mmol of a solution prepared by adding acetyl bromide (22 μL) to MeOH (1 mL) in a dry Schlenk tube, The mixture was stirred for 30 min at r.t. before removing the solvent in vacuo to give the catalyst. Method 3: To a dried microwave tube was added benzeneruthenium chloride dimer (1.7 mg, 0.0034 mmol) and
- 10

18
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22
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- General Procedure for Catalytic Hydrogenation: An autoclave containing a reaction vial charged with catalyst and stirring bead was charged with diketone 1 (0.34 mmol, Anhydrous degassed solvent was added to the vial under an N2 atmosphere. The autoclave was sealed, flushed with hydrogen, and brought to the initial pressure (50 bar) and stirred at 50°C for 16 h. The mixture was concentrated in vacuo and an NMR taken of the resulting solid. The product was recrystallised from CH2Cl 2 to give white needles. The anti/syn ratio was determined by 19F NMR and the ee value by HPLC. Compound, )-2a: [α]D20 +37.8 (c 1.14, MeOH, mp 180°C. 1H NMR (300 MHz, CDCl3, δ, 7.49-7.36 (10 H, m, ArH, 5.08 (2 H, td J, 13, 4 Hz, CHOH, 3.10 (2 H, d J, 4 Hz, CHOH) ppm. 13C NMR (75 MHz, CDCl3, δ, 138.8 ArC, 128
- R = 19.84 [(+)-enantiomer], 34.24 [(-)-enantiomer], 37.52 (syn) min.

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