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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
Author(s) -
Kim CheolEui,
Park Youngchul,
Park Sangjune,
Lee Phil Ho
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400604
Subject(s) - chemistry , rhodium , acetal , sulfonyl , catalysis , ring (chemistry) , medicinal chemistry , combinatorial chemistry , stereochemistry , organic chemistry , alkyl
Diastereoselective synthesis of tetrahydro‐furanodihydropyrroles and tetrahydropyranodihydropyrroles containing N , O ‐acetal moieties is reported via rhodium‐catalyzed denitrogenative transannulation of N ‐sulfonyl‐1,2,3‐triazoles with oxacycloalkenes. A multitude of functionalized pyrroles possessing hydroxyalkyl group at C3‐position could be prepared via 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.