Kevin Arendt - Double Diastereoselective, Nucleophile-Catalyzed Aldol Lactonizations (NCAL) Leading to Beta-Lactone Fused Carbocycles and Extensions to Beta-Lactone Fused Tetrahydrofurans

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      Publication Details (including relevant citation   information):

      Morris, K. A.; Arendt, K. M.; Oh, S. H.; Romo, D. Org.   Lett. 2010. ASAP.

      Abstract:

      A double diastereoselective variant of the   nucleophile-catalyzed aldol lactonization (NCAL) process is   described. This strategy delivers beta-lactone-   fused carbocycles with good to excellent diastereoselectivities   using cinchona alkaloid catalysts with enantioenriched aldehyde   acids, which gave low diastereoselectivity based on substrate   control alone. beta-Lactone-fused   tetrahydrofurans are also prepared for the first time via the   NCAL process; however, diastereoselectivity was only modestly   improved when applying double diastereodifferentiation to these   systems.

      Address (URL): http://pubs.acs.org/doi/abs/10.1021/ol101388h