Synfacts 2009(6): 0646-0646  
DOI: 10.1055/s-0029-1217156
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Domino Prins-Friedel-Crafts Reaction

Contributor(s): Mark Lautens, Praew Thansandote
U. C. Reddy, S. Bondalapati, A. K. Saikia*
Indian Institute of Technology, Guwahati, India
Further Information

Publication History

Publication Date:
25 May 2009 (online)

Significance

An efficient synthesis of unsymmetrical 2,6-disubstituted 4-aryltetrahydropyrans is described using a domino Prins-Friedel-Crafts ­reaction. The scope includes a large variety of ­aryl, heteroaryl, and aliphatic aldehydes, and ­several neutral and electron-rich arenes. Extension to ­ketone substrates creates spirocyclic compounds in moderate yields.