Asymmetric one-pot four-component coupling reaction: Synthesis of substituted tetrahydropyrans catalyzed by diphenylprolinol silyl ether

Article abstract of DOI:10.1002/anie.201005386

(Chemical Equation Presented) Domino effect: The title reaction uses an asymmetric Michael/Henry reaction/acetalization/Lewis acid mediated allylation reaction to provide highly substituted tetrahydropyrans with excellent enantioselectivity (see scheme; TMS=trimethylsilyl). All the carbon atoms in the tetrahydropyran ring are substituted with different groups, and the relative and absolute stereochemistry of the five contiguous carbon centers are completely controlled.