Synthetic studies on quinine: quinuclidine construction via a Ketone Enolate regio-and diastereoselective Pd-mediated allylic alkylation

DM Johns, M Mori, RM Williams

Index: Johns, Deidre M.; Mori, Makoto; Williams, Robert M. Organic Letters, 2006 , vol. 8, # 18 p. 4051 - 4054

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Citation Number: 28

Abstract

7-Hydroxy-quinine was synthesized by an asymmetric aldol reaction that establishes the C8 and C9 stereochemistry, followed by construction of the 3-vinyl-quinuclidine azabicyclo [2.2. 2] octane by C3-C4 ring closure using an intramolecular palladium-mediated allylic alkylation with excellent regio-and diastereoselectivity. This is the first report of a ketone- enolate-stereocontrolled allylic alkylation mediated by palladium. The title compound and ...