1. Sequential Birch reduction-allylation/Cope rearrangement for the enantioselective construction of carbocyclic quaternary stereogenic centers
William P. Malachowski, Department of Chemistry , Bryn Mawr College, Bryn Mawr, PA
Reactions to extend the utility of chiral 4,4-disubstituted 2-cyclohexenones were explored, including conjugate addition and reductive-alkylation. The chiral 4,4-disubstituted 2-cyclohexenones, such as 1, were readily available from the Birch-Cope sequence, a process developed in our lab with ACS-PRF support. The combination of conjugate addition and alkylation reactions with the Birch-Cope sequence will afford exciting new avenues to efficiently construct bioactive natural products, which are an important source of inspiration for new medical therapies.
The Birch-Cope Sequence
Extending and Applying the Birch-Cope Sequence