Copper-Catalyzed Intramolecular Aldehyde-Ketone Nucleophilic Additions for the Synthesis of Chromans Bearing a Tertiary Alcohol Motif.

The synthesis of chroman-3-ol derivatives via intramolecular nucleophilic additions has been established. Aldehydes can be used as alkyl carbanion equivalents via reductive polarity reversal which is facilitated by a copper catalyst and N-heterocyclic carbene ligand under mild conditions. The key to success is the difference in reaction activity between aldehydes and ketones. Finally, this methodology also can be used to construct other cyclic structures containing tertiary alcohols including tetraline, cyclohexane, indan, and 9,10-dihydrophenanthrene.