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Journal Article
Research Support, Non-U.S. Gov't
Direct Access to 2,3,4,6-Tetrasubstituted Tetrahydro-2H-pyrans via Tandem S N 2'-Prins Cyclization.
Organic Letters 2017 September 16
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 SN 2'-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 SN 2' reaction as a preliminary step in the Prins cyclization.
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