Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 50, Pages 16694-16706Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201404668
Keywords
allenes; asymmetric catalysis; copper; Grignard reagents; P ligands
Categories
Funding
- Swiss National Research Foundation [200020-126663]
- Swiss National Science Foundation (SNF) [200020_126663] Funding Source: Swiss National Science Foundation (SNF)
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An easy and versatile Cu-catalyzed propargylic substitution process is presented. Using easily prepared prochiral dichloro substrates, readily available Grignard reagents together with catalytic amount of copper salt and chiral ligand, we accessed a range of synthetically interesting tri-substituted chloroallenes. Substrate scope and nucleophile scope are broad, providing generally high enantioselectivity for the desired 1,3-substitution products. The enantio-enriched chloroallenes could be further transformed into the corresponding trisubstituted allenes or terminal alkynes bearing all-carbon quaternary stereogenic centers, through the copper-catalyzed enantiospecific 1,1/1,3-substitutions. The two successive copper-catalyzed reactions could be eventually combined into a one-pot procedure and different desired allenes or alkynes were obtained respectively with high enantiomeric excesses.
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