In the THIQ of it:N-Alkyl tetrahydroisoquinolines are oxidatively coupled with a variety of nucleophiles in the presence of m-CPBA and [VO(acac)₂]. This method has been applied to the synthesis of the opioid methopholine

S2General. All reactions were carried out under Ar in glassware dried with a heat gun under vacuum (Schlenk line). The solvents were purified by distillation over the indicated drying agents and were transferred under Ar: THF, Et 2 O (Mg/anthracene), acetone (B 2 O 3 ), toluene (Na/K), CH 2 Cl 2 (CaH 2 ), MeOH (Mg, stored over 3Å MS); DMSO, DMF, CH 3 CN, NEt 3 and pyridine were dried by an adsorption solvent purification system based on molecular sieves. Unless stated otherwise, all commercially available compounds (ABCR, Acros, Aldrich, Strem, TCI) were used as received. [(Cp*RuCl) 4 ] was prepared according to a literature procedure and was stored under Argon. 1 Thin layer chromatography (TLC): Macherey-Nagel precoated plates (POLYGRAM® SIL/UV254); Flash chromatography: Merck silica gel 60 (40-63 μm) with predistilled or HPLC grade solvents; IR: ALPHA spectrometer (Bruker), wavenumbers (ṽ) in cm -1 . MS (EI): Finnigan MAT 8200 (70 eV), ESIMS: ESQ 3000 (Bruker), accurate mass determinations: Bruker APEX III FT-MS (7 T magnet) or MAT 95 (Finnigan); Optical rotations ([ ] ) were measured with a Perkin-Elmer Model 343 polarimeter.NMR: Spectra were recorded on a Bruker AV 400, AV 500 or AV 600 spectrometer in the solvents indicated; chemical shifts (δ) are given in ppm relative to TMS, coupling constants (J) in Hz. The solvent signals were used as references and the chemical shifts converted to the TMS scale (CDCl 3 at 7.26 and 77.16 ppm, CD 3 OD at 3.31 ppm and 49.00 ppm for 1 H and 13 C NMR spectroscopy, respectively).Where indicated, the signal assignments in the NMR spectra are unambiguous; the numbering scheme is arbitrary as shown in the inserts.(R)-Oct-1-en-3-ol (4). Novozyme (300 mg) was added to a solution of (±)-oct-1-en-3-ol (8.0 mL, 6.6 g, 52 mmol) and vinyl acetate (18.0 mL, 194 mmol) in hexane (70 mL) and the resulting suspension was gently stirred (~ 50 rpm) at ambient temperature. The progress of the reaction was monitored by GC-MS. After 42 h the immobilized enzyme was filtered off and rinsed with hexane (4 x 10 mL) and the combined filtrates were concentrated under reduced pressure. Purification of the residue by flash chromatography (hexane/tert-butyl methyl ether, 9:1 → 1:1) yielded the product as colorless liquid with a mushroom-like odor (2.27 g, 34%). The physical properties of the product were in full accordance with the literature; 2 the enantiomeric excess (> 99% ee) was determined by gas chromatography using a chiral stationary phase, cf: 1 P.

This discussion is centralized around an incident that took place in the Belgian village Witry the 17th of September 2014. A tractor accident led to the discharge of an aqueous solution of the herbicide metazachlor into the creek Moyémont that further merges into the river Sûre. About 20 km downstream, these waters supply the lake of the Upper-Sûre in Luxembourg, the biggest artificial lake and the main drinking water reservoir in the country. The evolution of the concentration of metazachlor and its metabolite 479M08 was partially tracked down from the river Sûre to the dam situated in the east. At this location, the SEBES drinking water treatment plant has its raw water intake from the lake. After this incident, substantial pollution by the metazachlor breakdown product 479M08 of the lake and of some other groundwater sources in the Grand Duchy was revealed due to a strong monitoring program that was started by the national water authority (AGE). This was for example the case in the SEBES groundwater resource Scheidhof close to Luxembourg City. There is also the reason to assume that contamination by 479M08 existed already in the lake before the incident in Witry, certainly due to agricultural activity. In the second part of this discussion, these perceptions are placed in their appropriate political context. Indeed, the quality of groundwater and drinking water is strongly regulated in the European Union and in Luxembourg. Compound 479M08, for instance, is submitted to a maximum parametric value of 0.1 µg/L in Luxembourg. Several short- and longtime political measures had to be taken to guarantee the wholesomeness of the water from a legal point of view.

General. All reactions were carried out under Ar in glassware dried with a heat gun under vacuum (Schlenk line). The solvents were purified by distillation over the indicated drying agents and were transferred under Ar: THF, Et 2 O (Mg/anthracene), acetone (B 2 O 3), toluene (Na/K), CH 2 Cl 2 (CaH 2), MeOH (Mg, stored over 3Å MS); DMSO, DMF, CH 3 CN, NEt 3 and pyridine were dried by an adsorption solvent purification system based on molecular sieves. Unless stated otherwise, all commercially available compounds (ABCR, Acros, Aldrich, Strem, TCI) were used as received. [(Cp*RuCl) 4 ] was prepared according to a literature procedure and was stored under Argon. 1 Thin layer chromatography (TLC): Macherey-Nagel precoated plates (POLYGRAM® SIL/UV254); Flash chromatography: Merck silica gel 60 (40-63 μm) with predistilled or HPLC grade solvents; IR: ALPHA spectrometer (Bruker), wavenumbers (ṽ) in cm-1. MS (EI): Finnigan MAT 8200 (70 eV), ESIMS: ESQ 3000 (Bruker), accurate mass determinations: Bruker APEX III FT-MS (7 T magnet) or MAT 95 (Finnigan); Optical rotations ([ ]) were measured with a Perkin-Elmer Model 343 polarimeter. NMR: Spectra were recorded on a Bruker AV 400, AV 500 or AV 600 spectrometer in the solvents indicated; chemical shifts (δ) are given in ppm relative to TMS, coupling constants (J) in Hz. The solvent signals were used as references and the chemical shifts converted to the TMS scale (CDCl 3 at 7.26 and 77.16 ppm, CD 3 OD at 3.31 ppm and 49.00 ppm for 1 H and 13 C NMR spectroscopy, respectively). Where indicated, the signal assignments in the NMR spectra are unambiguous; the numbering scheme is arbitrary as shown in the inserts. (R)-Oct-1-en-3-ol (4). Novozyme (300 mg) was added to a solution of (±)-oct-1-en-3-ol (8.0 mL, 6.6 g, 52 mmol) and vinyl acetate (18.0 mL, 194 mmol) in hexane (70 mL) and the resulting suspension was gently stirred (~ 50 rpm) at ambient temperature. The progress of the reaction was monitored by GC-MS. After 42 h the immobilized enzyme was filtered off and rinsed with hexane (4 x 10 mL) and the combined filtrates were concentrated under reduced pressure. Purification of the residue by flash chromatography (hexane/tert-butyl methyl ether, 9:1 → 1:1) yielded the product as colorless liquid with a mushroom-like odor (2.27 g, 34%). The physical properties of the product were in full accordance with the literature; 2 the enantiomeric excess (> 99% ee) was determined by gas chromatography using a chiral stationary phase, cf: 1

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