Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 59, Issue 3, Pages 1176-1180Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201912703
Keywords
allenes; copper; palladium; enantioselectivity; synthetic methods
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Funding
- National Nature Science Foundation of China [21871251, 21572218, 21472184]
- Biological Resources Programme, Chinese Academy of Sciences [KFJBRP-008]
- Sichuan SciTech Department [2016JZ0022, 2019YJ0471]
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A cooperative Cu/Pd-catalyzed enantioselective synthesis of multisubstituted allenes is established. By employing chiral sulfoxide phosphine (SOP)/Cu and PdCl2(dppf) complexes as catalysts, the 1,4-arylboration of 1,3-enynes provides an efficient approach to trisubstituted chiral allenes with up to 92 % yield and 97:3 er. Furthermore, by using 2-substituted 1,3-enynes as substrates, the tetrasubstituted chiral allenes were successfully generated using this strategy. Finally, theoretical calculations indicate that the transmetallation of the allenylcopper species is the rate-limiting step of this transformation.
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