Journal
TETRAHEDRON
Volume 72, Issue 21, Pages 2643-2648Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2015.05.035
Keywords
Cinchona alkaloids; Sulfur nucleophiles; Epoxide ring opening; Carbon-sulfur bond formation
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Funding
- National Science Centre, Poland [2013/09/B/ST5/03410]
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A series of functional modules were regio- and stereoselectively attached to the Cinchona alkaloid scaffolds. The S(N)2 reactions of thiolates with alkaloid mesylate and epoxide introduced metal-complexing moieties, including the heterocyclic systems of pyridine and 1,10-phenanthroline. The respective H-bond donating thiourea and salane motifs were formed in an additional step. The modified Cinchona alkaloids were tested in the metal-catalyzed Henry and Tsuji-Trost reactions. (C) 2015 Elsevier Ltd. All rights reserved.
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