Enantioselective elimination reaction of a 6,6-membered bicyclic allylic carbonate. Importance of chirality reversal depending on the palladium-chiral phosphine ratio

Isao Shimizu, Yoshiyuki Matsumoto, Ken Shoji, Toshiya Ono, Akiharu Satake, Akio Yamamoto

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

Reaction of (±)-8α-methoxycarbonyloxy-4αβ-methyl-2,3,4,4a,5,6,7,8-octahydronap hthalene (1) in the presence of a palladium-chiral phosphine catalyst gave 4a-methyl-3,4,4a,5,6,7-hexahydronaphthalene (2) enantioselectively. When the reaction was carried out using Pd(OAc)2 and (S)-(-)-BINAP, the enantioselection was influenced by the phosphine to palladium ratio, because (S)-BINAP oxide generated in situ acted as a ligand causing the opposite enantioselectivity. High enantioselectivity (86% ee) was obtained when (1-Me-C3H5-PdCl)2 and (S)-(-)-p-Tol-BINAP were used.

Original languageEnglish
Pages (from-to)7115-7118
Number of pages4
JournalTetrahedron Letters
Volume37
Issue number39
DOIs
Publication statusPublished - 1996 Sep 23

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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