Application of nucleophile promoted Aldol lactonization to �-substituted substrates provides bicyclic �-lactones with excellent diastereoselectivities.  However, alternative substitution patterns lead to only moderate diastereoselectivity.  Thus a double diastereoselective variant was developed and applied to carbocycle substrates.  Dioxabicyclo[3.2.0]heptanones were also explored and show promise under varied reaction conditions.

Double diastereoselective, nucleophile catalyzed Aldol lactonizations (NCAL) leading to β-lactone fused carbocycles and tetrahydrofurans

240th National Meeting (2010)

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