title: Double diastereoselective, nucleophile-catalyzed aldol lactonizations (NCAL) leading to beta-lactone fused carbocycles and extensions to beta-lactone fused tetrahydrofurans.
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.
authors: Department of Chemistry, Texas A&M University, P.O. Box 30012, College Station, Texas 77842-3012, USA.
authors: Kay A
authors: KA
authors: Morris
authors: Kevin M
authors: KM
authors: Arendt
authors: Seong Ho
authors: SH
authors: Oh
authors: Daniel
authors: D
authors: Romo
mesh_terms: D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D002930:Cinchona Alkaloids; D005663:Furans; D007783:Lactones