Asymmetric synthesis of bicyclic beta-lactones via the intramolecular, nucleophile-catalyzed aldol lactonization: improved efficiency and expanded scope.

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.

Cite this paper

@article{Oh2005AsymmetricSO, title={Asymmetric synthesis of bicyclic beta-lactones via the intramolecular, nucleophile-catalyzed aldol lactonization: improved efficiency and expanded scope.}, author={Seong Ho Oh and Guillermo S Cortez and Daniel Romo}, journal={The Journal of organic chemistry}, year={2005}, volume={70 7}, pages={2835-8} }