Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 58, Issue 40, Pages 14219-14223Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201909151
Keywords
Grignard reagent; heterocycles; olefins; spiro compounds; titanium
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Funding
- DAAD [57386699]
- Rice University
- National Institutes of Health [R01 GM-114609-04]
- National Science Foundation (CAREER:-SusChEM) [CHE-1546097]
- Robert A. Welch Foundation [C-1764]
- Amgen
- Biotage
- National Science Foundation [1842494]
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The Ti-IV-mediated synthesis of spirocyclic NH-azetidines from oxime ethers using either an alkyl Grignard reagent or terminal olefin ligand exchange coupling partner is described. Through a proposed Kulinkovich-type mechanism, a titanacyclopropane intermediate forms and serves as a 1,2-aliphatic dianion equivalent, inserting into the 1,2-dielectrophilc oxime ether to ultimately give rise to the desired N-heterocyclic four-membered ring. This transformation proceeds in moderate yield to furnish previously unreported and structurally diverse NH-azetidines in a single step.
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