caesium carbonate in N,N-dimethyl-formamide T=75°C; 18 h;

triethylsilane; AlCl3, aluminium chloride in dichloromethane; acetonitrile T=20 - 30°C; 1 h; Product distribution / selectivity;

1: (S)-4-iodo-1-chloro-2-(4-tetrahydrofuran-3-yloxy-benzyl)-benzene With isopropylmagnesium chloride; lithium chloride in tetrahydrofuran T=-21 - -15°C; 1.83333 h; 2: (3R,4S,5R,6R)-3,4,5-tris((trimethylsilyl)oxy)-6-(((trimethylsilyl)oxy)methyl)tetrahydro-2H-pyran-2-one in dichloromethane; acetonitrile T=-25 - -13°C; 2.91667 h;

triethylsilane; boron trifluoride diethyl etherate in dichloromethane; acetonitrile T=-20 - 10°C; 2 h; Product distribution / selectivity;

1.1: oxalyl dichloride / N,N-dimethyl-formamide / 5 h / 25 - 30 °C 1.2: 6 h / 20 - 30 °C 2.1: potassium tert-butylate / tetrahydrofuran / 4 h / 16 - 25 °C 2.2: 1.83 h / 20 - 21 °C 3.1: AlCl3, aluminium chloride; 1,1,3,3-tetramethyldisiloxane / toluene / 2.5 h / 18 - 26 °C 4.1: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1.83 h / -21 - -15 °C 4.2: 2.92 h / -25 - -13 °C View Scheme

1.1: oxalyl dichloride / N,N-dimethyl-formamide / 5 h / 25 - 30 °C 1.2: 6 h / 20 - 30 °C 2.1: potassium tert-butylate / tetrahydrofuran / 4 h / 16 - 25 °C 2.2: 1.83 h / 20 - 21 °C 3.1: AlCl3, aluminium chloride; 1,1,3,3-tetramethyldisiloxane / toluene / 2.5 h / 18 - 26 °C 4.1: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1.83 h / -21 - -15 °C 4.2: 2.92 h / -25 - -13 °C View Scheme

1.1: potassium tert-butylate / tetrahydrofuran / 4 h / 16 - 25 °C 1.2: 1.83 h / 20 - 21 °C 2.1: AlCl3, aluminium chloride; 1,1,3,3-tetramethyldisiloxane / toluene / 2.5 h / 18 - 26 °C 3.1: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1.83 h / -21 - -15 °C 3.2: 2.92 h / -25 - -13 °C View Scheme

1.1: AlCl3, aluminium chloride; 1,1,3,3-tetramethyldisiloxane / toluene / 2.5 h / 18 - 26 °C 2.1: isopropylmagnesium chloride; lithium chloride / tetrahydrofuran / 1.83 h / -21 - -15 °C 2.2: 2.92 h / -25 - -13 °C View Scheme