Dr. Michael Prein and Prof. Dr. Waldemar Adam
The obstinate singlet oxygen can be tamed by a number of factors: steric, stereoelectronic, electronic, and conformational effects of the functional group X play an important role in controlling the direction of the attack of singlet oxygen on alkenes [Eq. (a)]. This unfortunately rarely employed reaction, the Schenck ene reaction, yields diastereoselectively oxyfunctionalized compounds—useful intermediates in organic synthesis. X = hydroxyl, amino, halogen, ether, ester, sulfoxide, sulfone.