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Access to Highly Functionalized Sulfonated Cyclopentanes by Acid‐Promoted Rauhut–Currier Reaction with Sulfinamides
Author(s) -
Gigant Nicolas,
Drège Emmanuelle,
Retailleau Pascal,
Joseph Delphine
Publication year - 2015
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.201502816
Subject(s) - cyclopentanes , chemistry , catalysis , organic chemistry
An unexpected acid‐mediated cascade reaction induced by conjugate addition of sulfinamides to dienediones has been developed. This highly efficient Rauhut–Currier reaction enables the rapid, high‐yielding construction of sulfonated cyclopentanes with three contiguous stereogenic centers in a single operation starting from simple sulfinamides. This process constitutes the first example of sulfinamide‐promoted cycloisomerization.