Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 55, Issue 49, Pages 15406-15410Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201609853
Keywords
aminocyclopropanes; asymmetric catalysis; cyclopropenes; hydroamination; lanthanide complexes
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Funding
- JSPS [26220802]
- Grants-in-Aid for Scientific Research [26220802] Funding Source: KAKEN
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The search for efficient and selective routes for the synthesis of chiral aminocyclopropane derivatives is of great interest and importance as these structures are important components of biologically active natural products and pharmaceuticals. We herein report the enantioselective intermolecular hydroamination of substituted cyclopropenes with various amines catalyzed by chiral half-sandwich rare-earth-metal complexes. This method constitutes a 100% atom-efficient route for the synthesis of a variety of chiral -aminocyclopropane derivatives in high yields (up to 96%) and excellent stereoselectivity (up to >20:1 d.r. and 99% ee) under mild reaction conditions (25 degrees C).
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