4.8 Article

Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow-Generated Diazo Compounds and Propargylated Amines

期刊

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 56, 期 7, 页码 1864-1868

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201611067

关键词

allenes; asymmetric catalysis; copper; diazo compounds; flow chemistry

资金

  1. Cambridge Home and European Scholarship Scheme
  2. Erasmus Scholarship Scheme
  3. Swiss National Science Foundation
  4. UCB Biopharma SPRL
  5. EPSRC [EP/ K009494/1, EP/ K039520/1, EP/ M004120/1]
  6. EPSRC [EP/K009494/1, EP/K039520/1, EP/M004120/1] Funding Source: UKRI
  7. Engineering and Physical Sciences Research Council [EP/M004120/1, EP/K009494/1] Funding Source: researchfish

向作者/读者索取更多资源

We report herein the asymmetric coupling of flow-generated unstabilized diazo compounds and propargylated amine derivatives, using a new pyridinebis(imidazoline) ligand, a copper catalyst and base. The reaction proceeds rapidly, generating chiral allenes in 10-20 minutes with high enantioselectivity (89-98% de/ee), moderate yields and a wide functional group tolerance.

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