1: With borane-THF; (S)-proline (R)-1,1'-bi(2-naphthyl)dioxyboryl ester in tetrahydrofuran T=0 - 5°C; 48 h; 2: With hydrogenchloride in tetrahydrofuran Title compound not separated from byproducts;

1: With borane-THF; (S)-proline (R)-1,1'-bi(2-naphthyl)dioxyboryl ester in tetrahydrofuran T=0 - 5°C; 48 h; 2: With hydrogenchloride in tetrahydrofuran Title compound not separated from byproducts;

1: With borane-THF; (S)-proline (R)-1,1'-bi(2-naphthyl)dioxyboryl ester in tetrahydrofuran T=0 - 5°C; 48 h; 2: With hydrogenchloride in tetrahydrofuran Title compound not separated from byproducts;

in hexane 2.5 h; Irradiation;

1: AgNO2; dipotassium peroxodisulfate; palladium (II) trifluoroacetate / 1,2-dichloro-ethane / 48 h / 110 °C / |Schlenk technique; |Sealed tube 2: hydrogenchloride; water / dichloromethane / 24 h / 100 °C / |Sealed tube View Scheme