LEWIS ACID PROMOTED PRINS CYCLIZATION USING NON-CONJUGATED DIENE ALCOHOL: SEQUENTIAL REACTIONS TERMINATED BY FLUORIDE ION

The sequential cyclization involving Prins cyclization was successfully demonstrated, in which the various aldehydes bearing the alkyl or aromatic substituent were reacted with the alcohol bearing the non-conjugated diene moiety in the presence of 2 equiv. of BF3 center dot Et2O and 4 mol% of TMSC1 at -40 degrees C to afford the corresponding fluorinated bicyclic compounds in moderate to good yields.