Sultines as o-Quinodimethane Precursors in an Oxa-Diels –Alder Reaction: Synthesis of Functionalized Isochromans

Synlett DOI: 10.1055/a-2236-9589 The development of an oxa-Diels–Alder reaction between sultines and carbonyl compounds is reported. o-Quinodimethanes, generated from sultines, undergo a [4+2]-cycloaddition with activated aldehydes or ketones in the presence of Cu(OTf)2 to provide a variety of functionalized isochromans, including spiroisochromans, in up to 99% yield. The developed protocol demonstrates broad functional-group compatibility and tolerates unprotected isatins bearing free NH-functionalities. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Synlett - January 31, 2024 Category: Chemistry Authors: Ngamnithiporn, Aurapat Chuentragool, Padon Songthammawat, Poramate Punnita, Supakarn Photong, Kittithuch Ploypradith, Poonsakdi Ruchirawat, Somsak Tags: letter Source Type: research