4.5 Article

Hydroxy-Directed Cyclopropanation of Esters: Synthesis of Trisubstituted Cyclopropanols

Journal

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2014, Issue 1, Pages 181-187

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201301252

Keywords

Small ring systems; Allylic compounds; Titanium; Grignard reaction; Synthetic methods

Funding

  1. National Science Foundation (NSF) [CHE-1212879]
  2. Division Of Chemistry
  3. Direct For Mathematical & Physical Scien [1265843] Funding Source: National Science Foundation

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The Kulinkovich cyclopropanation of esters with disubstituted homoallylic alcohols is described for the preparation of 1,2,3-trisubstituted cyclopropanols. Central to the successful implementation is the generation in situ of a temporary alkoxy tether between a homoallylic alcohol and an alkoxytitanium species to override unfavorable steric factors.

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