Publication Details (including relevant citation information):
Morris, K. A.; Arendt, K. M.; Oh, S. H.; Romo, D. Org. Lett. 2010. ASAP.
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