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Rhodium‐Catalyzed Denitrogenative [2,3] Sigmatropic Rearrangement: An Efficient Entry to Sulfur‐Containing Quaternary Centers
Author(s) -
Yadagiri Dongari,
Anbarasan Pazhamalai
Publication year - 2013
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201302653
Subject(s) - regioselectivity , cycloaddition , rhodium , chemistry , catalysis , alkyl , combinatorial chemistry , sulfonyl , sigmatropic reaction , sulfur , medicinal chemistry , organic chemistry
Chemical building blocks : α‐Sulfenylated imines containing a quaternary center, an ubiquitous subunit and excellent building block, were achieved by rhodium‐catalyzed denitrogenative [2,3] sigmatropic rearrangements of N ‐sulfonyl‐1,2,3‐triazoles with allylaryl(alkyl) sulfides. Coupling of this methodology with a copper‐catalyzed cycloaddition reaction provides a platform for the direct regioselective functionalization of alkynes (see scheme; TC=thiophenecarboxylate; Ts= p ‐toluenesulfonyl).