Diastereoselective Synthesis of Six‐Membered Carbocyclic Spirooxindoles via 6π‐Electrocyclization of 3‐Dienylidene‐2‐ oxindoles. Issue 7 (29th April 2015)

• Record Type: Journal Article
• Authors: Kim, Ko Hoon; Moon, Hye Ran; Lee, Junseong; Kim, Jimin; Kim, Jae Nyoung
• Is Part Of: Advanced synthesis & catalysis. Volume 357:Issue 7(2015)
• Page Start: 1532
• Page End: 1544
• Publication Date: 2015-04-29
• Subjects: Catalysis -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Chemistry -- Periodicals; Chemistry, Technical -- Periodicals; Chemistry -- Periodicals; Catalysis -- Periodicals; Technology, Pharmaceutical -- Periodicals; 547.2
• DOI: 10.1002/adsc.201500260
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The Wittig reaction of isatin derivatives with Morita–Baylis–Hillman bromides of cinnamaldehydes afforded 3‐dienylidene‐2‐oxindoles. These trienes were converted into the corresponding spirooxindoles in a stereoselective manner in refluxing toluene in good yields. The diastereomeric spirooxindoles could be obtained stereoselectively by adding a catalytic amount of palladium(II) acetate <italic>via</italic> the palladium‐catalyzed isomerization of <italic>EEE</italic>‐trienes to <italic>ZEE</italic>‐trienes followed by a more facile 6π‐electrocyclization process. The obtained spirooxindoles could be further functionalized by palladium‐catalyzed oxidative arylation, thionation with Lawesson's reagent, catalytic hydrogenation and Friedel–Crafts‐type reaction.</p> <p> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgjkt636x8" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </p> </abstract>