The construction of enantioselective quaternary centers is important to build methods to synthesize natural products and novel complex molecules targeted to address the need to overcome systemic acquired resistance of antibiotics, increase selectivity of designed therapeutic medicine, or to mechanistically outwit mutating cancer cells. By construction of quaternary stereocenters with adjacent vicinal tertiary functionalization we explored an efficient synthetic scheme via a tandem Cope Rauhut Currier reaction. The Birch Cope sequence is utilized in an enantioselective dual alkyl functionalization of an quaternary carbon for construction of hexahydronaphthalene core molecule (1 ). This approach was utilized to explore techniques for natural product synthesis. 

Curious Cope rearrangement in an enantioselective synthesis

244th National Meeting (2012)

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