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Enantioselective synthesis of 1,2-disubstituted thiocyclobutanes via Michael addition
Emma G L Robert1, Jerome Waser1
1Laboratory of Catalysis and Organic Synthesis, Institute of Chemical Sciences and Engineering, Ecole Polytechnique Fédérale de Lausanne 1015 Lausanne Switzerland jerome.waser@epfl.ch.
None:
We report the diastereoselective and enantioselective synthesis of thio-substituted cyclobutanes via a sulfa-Michael addition using cyclobutenes. In the presence of DBU, various thio-cyclobutane esters and amides were obtained in up to quantitative yield and >95 : 5 dr. Using a chiral chinchona-based squaramide bifunctional acid-base catalyst and an N-acyl-oxazolidinone-substituted cyclobutene, thio-cyclobutanes were obtained with high yield and enantioselectivity (er up to 99.7 : 0.3).
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