24463-33-0Relevant articles and documents
Enantioselective Conversion of Achiral Cyclohexadienones to Chiral Cyclohexenones by Desymmetrization
Han, Yixin,Breitler, Simon,Zheng, Shao-Liang,Corey
supporting information, p. 6172 - 6175 (2016/12/09)
The enantioselective reduction of prochiral 4,4-disubstituted 2,5-cyclohexadienones to chiral 2-cyclohexenones has been accomplished by the use of a carefully selected chiral bisphosphine-CuI complex and diisobutylaluminum hydride-hexamethylphosphoric triamide complex. This reagent has provided access to a key bicyclic intermediate for the total synthesis of the natural enantiomer of the pentacyclic sesterterpene retigeranic acid that involves spatial discrimination between CH3 and CH2CH2R substituents, an operation that has been elusive previously. In addition, a second method for desymmetrization is described using catalytic enantioselective [4 + 2]-cycloaddition of cyclopentadiene to prochiral 4,4-disubstituted 2,5-cyclohexadienones.