Enantioselective Michael addition catalyzed by an optically active 1-chlorovinyl cobalt(III) complex

Tatsuyuki Tsubo, Tohru Yamada

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

Abstract The optically active 1-chlorovinyl cobalt(III) complex was prepared from the ketoiminatocobalt(II) complex upon treatment with sodium borohydride in the presence of 1,1,1-trichloroethane. The obtained complex was found to catalyze the enantioselective Michael addition of various malonates on cyclic or acyclic enones to afford the corresponding adduct. In this reaction, the use of sodium alkoxide as a base with 1-chlorovinyl cobalt(III) complex catalyst was crucial to improving both the reactivity and enantioselectivity.

Original languageEnglish
Pages (from-to)1111-1115
Number of pages5
JournalSynlett
Volume26
Issue number8
DOIs
Publication statusPublished - 2015 Mar 9

Fingerprint

Cobalt
Malonates
Enantioselectivity
Sodium
Catalysts
1,1,1-trichloroethane
sodium borohydride

Keywords

  • cobalt catalysis
  • enantioselective reaction
  • enone
  • malonate
  • Michael addition

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Enantioselective Michael addition catalyzed by an optically active 1-chlorovinyl cobalt(III) complex. / Tsubo, Tatsuyuki; Yamada, Tohru.

In: Synlett, Vol. 26, No. 8, 09.03.2015, p. 1111-1115.

Research output: Contribution to journalArticle

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N2 - Abstract The optically active 1-chlorovinyl cobalt(III) complex was prepared from the ketoiminatocobalt(II) complex upon treatment with sodium borohydride in the presence of 1,1,1-trichloroethane. The obtained complex was found to catalyze the enantioselective Michael addition of various malonates on cyclic or acyclic enones to afford the corresponding adduct. In this reaction, the use of sodium alkoxide as a base with 1-chlorovinyl cobalt(III) complex catalyst was crucial to improving both the reactivity and enantioselectivity.

AB - Abstract The optically active 1-chlorovinyl cobalt(III) complex was prepared from the ketoiminatocobalt(II) complex upon treatment with sodium borohydride in the presence of 1,1,1-trichloroethane. The obtained complex was found to catalyze the enantioselective Michael addition of various malonates on cyclic or acyclic enones to afford the corresponding adduct. In this reaction, the use of sodium alkoxide as a base with 1-chlorovinyl cobalt(III) complex catalyst was crucial to improving both the reactivity and enantioselectivity.

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KW - malonate

KW - Michael addition

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