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Ring‐Opening 1,3‐Aminochalcogenation of Donor–Acceptor Cyclopropanes: A Three‐Component Approach
Author(s) -
Augustin André U.,
Jones Peter G.,
Werz Daniel B.
Publication year - 2019
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.201902160
Subject(s) - electrophile , ring (chemistry) , cyclopropane , sulfonamide , succinimides , chemistry , catalysis , residue (chemistry) , acceptor , stereochemistry , selenium , medicinal chemistry , organic chemistry , physics , condensed matter physics
A 1,3‐aminothiolation was realized by reacting 2‐substituted cyclopropane 1,1‐dicarboxylates with sulfonamides and N ‐(arylthio)succinimides. Under Sn(OTf) 2 catalysis the transformation proceeded smoothly to the corresponding ring‐opened products bearing the sulfonamide in the 1‐position next to the donor and the arylthio residue in the 3‐position next to the acceptor. The procedure was extended to the corresponding selenium analogues by employing N ‐(phenylseleno)succinimides as an electrophilic selenium source.