Diastereoselectivity of the α,α-diphenylprolinol trimethylsilyl ether-catalyzed two-component domino reactions: toward cyclohexanes with six stereogenic centers

Theoretical calculations were employed to investigate the diastereoselectivity of the α,α-diphenylprolinol trimethylsilyl ether-catalyzed two-component cascade reactions between (i) pentane-1,5-dial and nitrostyrene, and (ii) pentane-1,5-dial and an α,β-unsaturated carbonyl compound. In both cases, the enol mechanism was able to account for the enantioselectivity of not only the major diastereomer formed, but also that of the minor diastereomers. Insights gained from our mechanistic investigations have enabled us to develop a scheme for the synthesis of cyclohexanes with six stereogenic centers, via two-component one-pot catalytic domino reactions.

Graphical abstractDownload full-size image