One-Pot Synthesis of 1-Substituted 1H-Isochromenes by Combining Brønsted Acid with Silver Catalysis

^§ These authors contributed equally to this work.

Dedicated to Professor Gerhard Bringmann on the occasion of his 65th birthday

Abstract

A one-pot synthesis of 1-substituted 1H-isochromenes employing various 2-alkynyl-benzaldehydes and ketones as substrates under a combination of Brønsted acid and silver catalysis has been developed. The isochromenes, which are present as important heterocyclic core structures in many bioactive and natural compounds, are obtained in medium to excellent yields with diastereomeric ratios of up to 9:1. A first enantioselective variant has also been tested.

Key words

isochromene - Brønsted acid catalysis - silver catalysis - organocatalysis - one-pot synthesis

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