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

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phosphine
Chirality
Carbonates
Palladium
Enantioselectivity
Oxides
Ligands
Catalysts
2-naphthol BINAP

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Enantioselective elimination reaction of a 6,6-membered bicyclic allylic carbonate. Importance of chirality reversal depending on the palladium-chiral phosphine ratio. / Shimizu, Isao; Matsumoto, Yoshiyuki; Shoji, Ken; Ono, Toshiya; Satake, Akiharu; Yamamoto, Akio.

In: Tetrahedron Letters, Vol. 37, No. 39, 23.09.1996, p. 7115-7118.

Research output: Contribution to journalArticle

Shimizu, Isao ; Matsumoto, Yoshiyuki ; Shoji, Ken ; Ono, Toshiya ; Satake, Akiharu ; Yamamoto, Akio. / Enantioselective elimination reaction of a 6,6-membered bicyclic allylic carbonate. Importance of chirality reversal depending on the palladium-chiral phosphine ratio. In: Tetrahedron Letters. 1996 ; Vol. 37, No. 39. pp. 7115-7118.
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