Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2013, Issue 18, Pages 3662-3666Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201300413
Keywords
Iodine; Hypervalent compounds; Ylides; Small ring systems
Categories
Funding
- Ministry of Education, Culture, Sciences, and Technology (MEXT), Japan
- Grants-in-Aid for Scientific Research [23390006, 25460016] Funding Source: KAKEN
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An ester exchange reaction of -butoxy--acyloxyvinyl-3-iodane with lithium bases (ROLi and nBuLi) efficiently generates highly labile monoester iodonium ylide at low temperature. The iodonium ylide generated in situ cleanly undergoes Darzens condensation with aromatic aldehydes to afford trans-epoxy ester selectively.
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