This work was supported by the Grants-in-Aid for Young Scientists (A), JSPS to H.O. and by CREST and ACT-C, JST to M.S. Y.M. thanks the JSPS for their scholarship support.
Copper-Catalyzed γ-Selective and Stereospecific Direct Allylic Alkylation of Terminal Alkynes: Synthesis of Skipped Enynes†
Article first published online: 9 APR 2013
Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Angewandte Chemie International Edition
Volume 52, Issue 20, pages 5350–5354, May 10, 2013
How to Cite
Makida, Y., Takayama, Y., Ohmiya, H. and Sawamura, M. (2013), Copper-Catalyzed γ-Selective and Stereospecific Direct Allylic Alkylation of Terminal Alkynes: Synthesis of Skipped Enynes . Angew. Chem. Int. Ed., 52: 5350–5354. doi: 10.1002/anie.201300785
- Issue published online: 3 MAY 2013
- Article first published online: 9 APR 2013
- Manuscript Received: 29 JAN 2013
- Grants-in-Aid for Young Scientists (A)
- allylic compounds;
- homogeneous catalysis;
- synthetic methods
Skipping out: The title reaction using internal secondary allylic phosphates proceeded with excellent γ regioselectivity and E stereoselectivity to give skipped enynes. Enantioenriched secondary allylic phosphates proceeded with 1,3-anti stereochemistry to afford the corresponding chiral 1,4-enynes, which were used for various derivatizations and the formal total synthesis of a GnRH antagonist. phen=1,10-phenanthroline.