Synthesis 2017; 49(06): 1243-1254
DOI: 10.1055/s-0036-1588641
paper
Georg Thieme Verlag Stuttgart · New York

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

Nina Felicitas Bröhl
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Dipti Sankar Kundu
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Gerhard Raabe
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
,
Dieter Enders*
Institute of Organic Chemistry, RWTH Aachen University, Landoltweg 1, 52074 Aachen, Germany   Email: enders@rwth-aachen.de
› Author Affiliations
Further Information

Publication History

Received: 10 October 2016

Accepted: 11 October 2016

Publication Date:
09 November 2016 (online)


§ 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.

Supporting Information

 
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