Substituted Cyclohexanes via a Highly Selective Domino Reaction

Significance

Hayashi and colleagues report a formal carbo [3+3] cycloaddition between α,β-unsaturated aldehydes 1 and 3-oxopentanedioate 2 to afford cyclohexenones 4. The reaction proceeds via iminium-catalyzed domino Michael addition and Knoevenagel condensation and affords the desired product with high enantioselectivity and as a single diastereomer (determined after an in situ reduction to 5). Various further transformations could be performed on the intermediate 4 in the same pot to give functionalized cyclohexanols and cyclohexanones in diastereomerically pure form and with >60% yields.