Journal
TETRAHEDRON
Volume 66, Issue 31, Pages 5801-5810Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.05.005
Keywords
Metal-free; Hypervalent iodine; Cyclopropanation; Cyclopropyl keto-esters; Iodonium ylide
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Funding
- KYTHERA Biopharmaceuticals, Inc. Calabasas, California
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Intramolecular cyclopropanation of alkenes occurs thermally with iodonium ylides in the absence of conventional metal catalysts such as Rh(II) and Cu(II). In rigid molecular systems conversions are near quantitative. A mechanism is proposed involving formal 2+2 cycloaddition followed by reductive elimination of PhI to yield the cyclopropane. (C) 2010 Elsevier Ltd. All rights reserved.
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