Copper-catalyzed γ-selective and stereospecific direct allylic alkylation of terminal alkynes: Synthesis of skipped enynes

Yusuke Makida, Yurie Takayama, Hirohisa Ohmiya, Masaya Sawamura

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)5350-5354
Number of pages5
JournalAngewandte Chemie - International Edition
Volume52
Issue number20
DOIs
Publication statusPublished - May 10 2013
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

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