Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 10, Pages 2721-2725Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201713329
Keywords
asymmetric synthesis; desymmetrization; diaryliodonium salts; Heck reaction; homogeneous catalysis
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Funding
- EPFL (Switzerland)
- Swiss National Science Foundation (SNSF)
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A copper-catalyzed enantioselective arylative desymmetrization of prochiral cyclopentenes with diaryliodonium salts was developed. In the presence of a catalytic amount of a chiral copper-bisoxazoline complex, which was generated in situ, the reaction of 4-substituted or 4,4-disubstituted cyclopent-1-enes with diaryliodonium hexafluoroarsenates afforded the chiral arylated products in good yields with excellent enantioselectivity. A cyclohexyl-containing Box ligand was essential for the high enantioselectivity. Transformation of the enantiomerically enriched adducts into other chiral building blocks is also documented.
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