FeCl3-catalyzed tandem Prins and Friedel-Crafts cyclization: a highly diastereoselective route to polycyclic ring structures

作者：Ghosh Arun K^*; Keyes Chad; Veitschegger Anne M

来源：Tetrahedron Letters, 2014, 55(30): 4251-4254.

DOI：10.1016/j.tetlet.2014.05.092

• FeCl3 catalysis
• Isochromene
• Prins cyclization
• Friedel-Crafts reaction
• CBS reduction

Catalytic FeCl3 in the presence of 4 A molecular sieves has been shown to effect highly diastereoselective tandem Prins and Friedel-Crafts cyclization of substituted (E/Z)-6-phenylhex-3-en-1-ol and a variety of aldehydes to provide a range of polycyclic compounds in good to excellent yields. The reaction of an enantioenriched alcohol with an aldehyde provided the cyclization product without loss of optical activity. Furthermore, a Lewis acid catalyzed ring opening resulted in functionalized tetralin derivatives with multiple chiral centers. Published by Elsevier Ltd.

• 出版日期2014-7-23