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Copper-Catalyzed Propargylic Substitution of Dichloro Substrates: Enantioselective Synthesis of Trisubstituted Allenes and Formation of Propargylic Quaternary Stereogenic Centers

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Published in Chemistry - A European Journal. 2014, vol. 20, no. 50, p. 16694-16706
Abstract 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 trisubstituted chloroallenes. Substrate scope and nucleophile scope are broad, providing generally high enantioselectivity for the desired 1,3-substitution products. The enantioenriched 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.
Keywords AllenesAsymmetric catalysisCopperGrignard reagentsP ligands
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Other version: http://doi.wiley.com/10.1002/chem.201404668
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Research groups Groupe Alexakis
Groupe Bürgi
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LI, Hailing et al. Copper-Catalyzed Propargylic Substitution of Dichloro Substrates: Enantioselective Synthesis of Trisubstituted Allenes and Formation of Propargylic Quaternary Stereogenic Centers. In: Chemistry - A European Journal, 2014, vol. 20, n° 50, p. 16694-16706. https://archive-ouverte.unige.ch/unige:43540

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Deposited on : 2014-12-16

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