Tandem Prins and Friedel–Crafts Cyclizations for the Stereo­selective Synthesis of trans-Fused Hexahydro-1H-benzo[g]isochromene Derivatives

Abstract

Aldehydes and ketones undergo smooth coupling with (4E)-3-benzyl-5-phenylpent-4-en-1-ol in the presence of scandium(III) triflate (10 mol%) and 4-toluenesulfonic acid (30 mol%) to give the corresponding trans-fused hexahydro-1H-benzo[g]isochromenes in good yields with excellent selectivity. This is the first example of the synthesis of a trans-fused hexahydro-1H-benzo[g]isochromene derivatives from an aldehyde and (4E)-3-benzyl-5-phenylpent-4-en-1-ol through tandem Prins and Friedel–Crafts cyclizations.

Keywords

cyclizations - aldehydes - ketones - coupling - tandem reactions - catalysis - isochromenes

• References and Notes


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