Robert K. Boeckman

Cyclic vinyl ether carbanions—II : Preparation and applications to the synthesis of carbonyl compounds

Abstract Conditions for metalation of a variety of cyclic vinyl ethers and reaction of the resulting carbanions with electrophiles are described. Effects of the vinyl ether structure on the relative rates of metalation are discussed. Applications of this methodology to the construction of various types of carbonyl compounds are presented.

The utility of silicon in organic synthesis : Annulation methodology and applications employing ⇌-trimethylsilyl vinyl ketones

Abstract New annulation methodology based upon the addition of diorganocuprates to ⇌,β-unsaturated ketones and regiospecific trapping of the resulting enolate with ⇌-trimethylsilyl vinyl ketones is presented. The stereochemical details of the process have been elucidated and are discussed. Application of this methodology to the synthesis of a variety of polycyclic ketone structures is described including applications to steroid synthesis.