Diastereoselective Synthesis of Tetrahydrofurano‐ and Tetrahydropyrano‐dihydropyrroles Containing N, O‐Acetal Moieties via Rhodium‐Catalyzed Transannulation of N‐Sulfonyl‐1, 2, 3‐triazoles with Oxacycloalkenes. Issue 1 (27th November 2014)

• Record Type: Journal Article
• Authors: Kim, Cheol‐Eui; Park, Youngchul; Park, Sangjune; Lee, Phil Ho
• Is Part Of: Advanced synthesis & catalysis. Volume 357:Issue 1(2015)
• Page Start: 210
• Page End: 220
• Publication Date: 2014-11-27
• 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.201400604
• Languages: English
• ISSNs: 1615-4150

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>Diastereoselective synthesis of tetrahydro‐furanodihydropyrroles and tetrahydropyranodihydropyrroles containing <italic>N</italic>, <italic>O</italic>‐acetal moieties is reported <italic>via</italic> rhodium‐catalyzed denitrogenative transannulation of <italic>N</italic>‐sulfonyl‐1, 2, 3‐triazoles with oxacycloalkenes. A multitude of functionalized pyrroles possessing hydroxyalkyl group at C3‐position could be prepared <italic>via</italic> Rh‐catalyzed denitrogenative transannulation/acid‐catalyzed ring‐opening reaction. A three component, one‐pot method is also achieved starting from terminal alkynes, tosyl azides, and dihydrofurans.</p> <p> <boxed-text content-type="graphic" position="anchor" orientation="portrait"> <graphic position="anchor" mimetype="image" xlink:href="ark:/27927/pgh31s3mmrq" orientation="portrait" xlink:type="simple" xmlns:xlink="http://www.w3.org/1999/xlink" /> </boxed-text> </p> </abstract>