Organic Letters
Organic Letters
5 years ago

Direct Access to 2,3,4,6-Tetrasubstituted Tetrahydro-2H-pyrans via Tandem SN2′–Prins Cyclization

Direct Access to 2,3,4,6-Tetrasubstituted Tetrahydro-2H-pyrans via Tandem SN2′–Prins Cyclization
Pedro O. Miranda, Sixto J. Pérez, Jimena Scoccia, Victoria Sinka, Víctor S. Martín, Juan I. Padrón, Daniel A. Cruz, Israel Fernández, Juan M. López-Soria
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02270

DOI: 10.1021/acs.orglett.7b02270

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