Jimena Scoccia, Sixto J Pérez, V. Sinka
Aug 31, 2017
Citations
0
Influential Citations
13
Citations
Journal
Organic letters
Abstract
A new, direct, and diastereoselective synthesis of activated 2,3,4,6-tetrasubstituted tetrahydro-2H-pyrans is described. In this reaction, iron(III) catalyzed an SN2'-Prins cyclization tandem process leading to the creation of three new stereocenters in one single step. These activated tetrahydro-2H-pyran units are easily derivatizable through CuAAC conjugations in order to generate multifunctionalized complex molecules. DFT calculations support the in situ SN2' reaction as a preliminary step in the Prins cyclization.