Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 25, Pages 6546-6549Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201403726
Keywords
reaction mechanisms; rearrangement; silanes; small ring system; synthetic methods
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Funding
- Ministry of Education, Culture, Sports, Science and Technology (Japan)
- Asahi Glass Foundation
- JSPS
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A potassium-bis(trimethylsilyl) amide-mediated cyclopropanation of allyl phosphates with silylboronates has been developed. Unlike the reported copper-catalyzed allylic substitution reactions, the nucleophile selectively attacks at the beta-position of the allylic substrates under the present reaction conditions. The mechanism of this process has also been investigated, thus indicating the involvement of a silylpotassium species as the active nucleophilic component.
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