Asymmetric Synthesis of Bicyclic β-Lactones via the Intramolecular, Nucleophile-Catalyzed Aldol Lactonization: Improved Efficiency and Expanded Scope
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TL;DR
The intramolecular, nucleophile-catalyzed, aldol lactonization (NCAL) process merges catalytic, asymmetric carbocycle synthesis with beta-lactone synthesis with greatly improved conversion and efficiency and shorter reaction times with no diminution of enantioselectivity.
Abstract
[reaction: see text] The intramolecular, nucleophile-catalyzed, aldol lactonization (NCAL) process merges catalytic, asymmetric carbocycle synthesis with beta-lactone synthesis. The application of modified Mukaiyama reagents to this process led to greatly improved conversion and efficiency (70-82% yield) and shorter reaction times with no diminution of enantioselectivity (91-98% ee). The process was extended to several new aldehyde-acid substrates leading to new bicyclic-beta-lactones. This methodology uniquely provides beta-lactone-fused cyclopentanes and cyclohexanes readied for further transformations.